Interview with a Barefoot Writer:
Don Hauptman


Don Hauptman

“Freelancers can readily generate new business by speaking and by writing content aimed at their target markets. I never cold called. When prospective clients contacted me, I always asked: ‘How did you find me?’ The answer: ‘I read your article’ or ‘I heard you speak.’ And sometimes: ‘I read your article and then I heard you speak.’”
— Don Hauptman, Master Copywriter

Don Hauptman’s 30- year career includes legendary campaigns such as the ad you might have seen for a foreign-language course: “Speak Spanish Like a Diplomat!” That headline is a classic and the ads generated tens of millions of dollars in sales.

Don is also the author of two wordplay books: Cruel and Unusual Puns (Dell, 1991) and Acronymania (Dell, 1993). He also wrote The Versatile Freelancer, an AWAI ebook that teaches copywriters how to diversify their careers into consulting, training, critiquing, and public speaking. I spoke with Don on a Tuesday morning from his home in New York City. Enjoy his candid and generous recommendations for succeeding as a copywriter, and note the many practical tips he offers new freelancers for generating business and branching out as a consultant.

Let’s start with your story — how did you become a copywriter?

I like to say that I have a mentor story. In the early 1970s, I was in the Navy. When I got out in 1974, I looked for a job with a Madison Avenue ad agency, or any sort of work in advertising or copywriting. But then as now, it was tough for someone with no experience to break in. So I did some freelance journalism, mainly for magazines covering small business and entrepreneurship.

Then a friend introduced me to Robert Kephart, the founder of what is now KCI Communications — one of the major financial newsletter publishers. Bob took a chance on me. I began doing a great deal of work for him, space ads and direct mail. I learned a lot because Bob was himself a skilled copywriter. The process of his critiquing drafts of my work was like graduate school in direct marketing and copywriting. So that first client transformed my whole life and career. I owe Bob quite a lot. Sadly, he died a few years ago.

So really, you were a freelancer from the start. How did you expand your business?

Bob generously began recommending me to other people who became my clients; you can’t beat referrals as a source of new business. Soon after, I joined the Newsletters Publishers Association, as it was then called, and my name became known via speaking at NPA’s conferences and other industry events. My career took off from there.

I did so much financial copywriting that, for a while, people called me “The Hard-Money Copywriter.” Hard money is the term for investments in gold and silver, Swiss banks, tax shelters — what wealthy people do with their dough.

Ever since I was a kid, maybe 10 years old, I was captivated by advertising. But I expected to one day work for one of those big agencies we see in the Mad Men series. It was that period — I grew up in the early 1960s. I never thought I’d be working at home as a freelancer. My parents were middle-class schoolteachers and that sort of life was unimaginable. I think I found, as many people do, that your career is something you can control to some extent, but it’s also in part the result of serendipity. I often reminded myself of that famous quotation, attributed to Pasteur: “Chance favors the prepared mind.” So I seized opportunities and made them work for me.

A few years ago, you retired from copywriting. What motivated that decision?

Several factors. One was the shift of marketing from print to the Internet. I love technology and the online world, but I’m really a print person at heart. I got a kick out of receiving samples of my direct-mail packages, the tangible nature of the experience, touching them and smelling them and such. Or looking at an issue of a magazine and finding an ad I wrote. It just isn’t the same online.

Not long before my decision to retire, a client asked me to do “keyword stuffing.” Your readers probably know what that is — sticking in words that appeal to search engines, even if they’re not especially appropriate in context. I thought, “We’re not writing for people anymore; we’re writing for robots and machines!” I don’t disparage technology and progress. In fact, it’s amazing what can be done online that we couldn’t do before. But the work was no longer as much fun as it had been. “Thirty years is a pretty good run,” I reasoned. “Perhaps it’s time to move on to other things.”

Such as? What are you doing these days?

For decades, I’ve had a parallel career writing about language — the English language, words, grammar, usage, and especially wordplay, what enthusiasts call “recreational linguistics.” In the early nineties, Dell published two of my books in this genre. I have ideas for other books. I’ve also written scores of articles on these subjects. Many of your readers may recall that for four and a half years, I wrote a column on language for Early to Rise, the popular e-zine.

So I figured I could cycle back to that passion — and disprove the aphorism of F. Scott Fitzgerald: “There are no second acts in American lives.” Maybe I do have a second act.

I still keep my hand in marketing, though. I like to teach and mentor younger copywriters, passing on what I’ve learned. I’ve spoken at AWAI conferences. There are people I’ve helped find jobs, start businesses, launch websites, that sort of thing. I do some pro bono work, consulting and advising on fundraising for causes I support: political and educational and cultural groups.

Last year, a former client approached me about writing the advertising for a high-tech launch and he invited me aboard on an equity basis. It could be another Google or Apple and make me a lot of money one day, though this sort of venture is always risky. But it reminded me of that mafiamovie line: “Just when you think you’re out, they pull you back in!”

So you’re keeping busy, in contrast to the boring retirement some people experience.

True, there’s plenty to occupy my time. A friend of mine was a college history professor for decades. He says, half-jokingly, “I had more free time before I retired!”

Returning to your copywriting career, what sort of clients did you write for?

I began with newsletters. And I also wrote promotions, mostly direct mail, for other information products such as magazines, books, conferences, seminars, and spoken-word audio. I had an epiphany one day, struck by the realization that information is what I knew how to sell. So it made one thing easy. If somebody called and said, “I need to promote a book” or a magazine or the like, I considered accepting the assignment. But if it were jewelry or perfume or vacuum cleaners, I politely declined and recommended another copywriter.

What were some of your biggest successes?

The campaign I’m probably best known for was a series of space ads, coupon ads, selling audiorecorded — cassettes at that time — foreign-language lessons. The headline was “Speak Spanish like a Diplomat!” There were courses in French, German, other languages too. You see, the tapes were originally created by the U.S. Foreign Service Institute to train diplomatic personnel. So that gave us a great hook. (Always find the product’s Unique Selling Proposition, which in this case was handed to me on a platter.) The ads ran everywhere and had total sales around $20 million. That’s the headline that, in all likelihood, will always be associated with my name. The campaign was written up in at least three college advertising textbooks. It even added a phrase to popular culture; I’ve seen riffs on it in all sorts of unexpected places.

Another campaign was for a newsletter called The Organized Executive: “How America’s Most Successful Executives Accomplish So Much in So Little Time.” It made me more money via royalties than anything I’ve written.

And I’m proud to have written the copy that launched Bob Kephart’s newsletter, Tax Angles. The carrier-envelope teaser was: “Counting on Your Tax Advisor to Help Cut Your Taxes? You’re Making the Most Expensive Mistake of Your Life!” I worked from Bob’s platform and his thinking was right on target. We tapped into a real need and concern of the prospect. The paid circulation reached 71,000. For a subscription newsletter, that’s a high number.

And which projects were your favorites?

As discussed, I was widely viewed as an expert in financial copywriting. And I did a lot of it. But that wasn’t what really excited me.

What I relished most was writing sales copy for publications about marketing. For example, I had a client who published a newsletter telling restaurateurs how to fill seats. Another was for hotel owners on generating more guests. I did others aimed at retailers, attorneys, accountants, doctors, dentists, and so on.

When I was writing promotional copy specifically about marketing and advertising, addressing how to sell, how to increase revenues, how to get publicity — that was great because, after all, that’s my own field and what I know best. I was sometimes able to suggest editorial ideas and even contribute a piece to the publication itself. So direct-mail pitches for those “how to market your business” newsletters were perhaps the most fun to write.

And I’ll note here a very different type of project that was an all-time favorite: Audio Classics, which made recordings of great books. Adam Smith, Jefferson, John Locke, Machiavelli — all those important books and authors we now wish we hadn’t been sleeping through when we were in school! I loved this assignment because I have a passion for learning, scholarship, the humanities. And bringing these works to a wide general audience was, in a way, a noble endeavor. I can’t prove this, but my hunch is that The Great Courses — formerly the Teaching Company — might not have launched or become successful had my client and I not proven decades ago that a market existed and that it could be done profitably.

It sounds like you covered a broad range of subject areas.

Yes, that’s a good point. There was so much variety in my clientele. I relished the excitement of tackling a newsletter or magazine or other information product in a whole new field. One day, I’m writing to chemical engineers … and then a week later, to educators or real-estate investors. That variety in itself was rewarding.

You started copywriting in the seventies. A lot has changed since then. What is one rule for good copywriting that was true when you started and that still holds true today?

There are many useful rules and principles, but I’ll mention one that I came up with early in my career. I immodestly called it Hauptman’s Law. It goes like this: “Start with the prospect, not with the product.” I think that alliterative formulation is original. But it’s simply a different way to express something we’ve all been taught: Focus on benefits, not features. There’s an earlier version that has a hypothetical homeowner saying to a salesman: “Don’t tell me about your grass seed; tell me about my lawn.” No matter how the idea is stated, the meaning is the same: Try to identify your target’s most important concerns, needs, wants, challenges, problems.

Because of the vast changes caused by new technology and the Internet, it’s easy to assume that everything is different and that the past is irrelevant. But really, basic human psychology and human nature have been the same for tens of thousands of years, and they’re not likely to evolve for many more millennia. So even though we’re clicking links on a tablet or smartphone instead of inserting an order form into a postal envelope, motivations and buying behavior are always going to be the same. As the song goes: “The fundamental things apply.”

Who has influenced your career the most? And what “must-reads” do you recommend for other writers?

Well, here I’m not terribly original. I cite the same influences and authors that most copywriters do. Eugene Schwartz’ Breakthrough Advertising is probably the single best book on copywriting ever written. I knew Gene. He was a philosopher as well as a copywriter, and that may be why this book is so deep, so profound, and why so many of its lessons are still valid and important. Certainly the books of Claude Hopkins, John Caples, and David Ogilvy are also at the top of my list.

You did a lot of speaking and writing about marketing and copywriting. Did you make any lasting contributions to these fields?

I hope I did. Two things are worth mentioning.

I constantly encounter discussions of “content marketing,” framing it as a hot new trend. This is where there’s an editorial component to the advertising — say, a tire company publishing an article online or making a video on how to reduce tread wear or the like. The idea is to lure people with free, valuable information, and then convert them to customers.

But it’s hardly new. My clients were publishers who learned how to repurpose or recycle their editorial material into their promotions. For example, a direct-mail letter for an investment newsletter might offer seven predictions for the economy and the market. Or it might say “Here are the five stocks to buy this year” and it wouldn’t just tease but would name the stocks. We see this also with health publications, where the advertising identifies the supplement to treat the affliction, thus offering real substance and value. You’re enticing the reader with helpful editorial content. But as I say, there’s nothing new about this. I think we were the pioneers. I didn’t invent the technique, but I was present at the creation. I did a lot of thinking about what makes it work and how to do it right, and I came up with a bunch of theories and guidelines.

Could you share one of them?

I’ll mention one principle, which applies to content marketing in all forums, whether print or online. It’s a mistake to assume you can simply excerpt or clone an editorial feature and just cut and paste it and it magically becomes your promotion. The material has to be tweaked and edited and rewritten for promotional purposes. That’s one reason copywriting skills are so important.

So content marketing is one area where I think I made a contribution, explaining what makes it work in presentations and articles for marketers over many years.

What’s the second contribution?

This has to do with market research. Again, so much of my work was with subscription publications that I’ll explain it in that context, though the principle has universal applications.

It’s common to see subscriber surveys with a long list of multiple-choice questions, asking the reader to rate each of the publication’s features on a scale from 1 to 10. Or the questions say, in effect, “What would you like us to write about?” But the problem with this approach is that it casts the reader in the role of an editor, which the reader is not. The better way is, again, to start with the prospect. You ask questions such as, “What’s your biggest problem right now in your job or industry?”

Today, decades after I began preaching this sermon, I still see people doing market research the wrong way. I recently attended a conference where participants received a long, multipage survey asking them to rate every speaker and event. Instead, the organizers might have asked “Why are you here? What did you most want to get out of the conference? Tell us if we succeeded — or where we let you down.” Still, at least some marketers practice the right approach.

You’re a big advocate of consulting. New writers often fear that they can’t do it because they don’t yet know enough. What’s a good way to gauge when you’re ready to teach and train others in, say, the specifics of persuasive writing?

I’ve done consulting and also corporate training, where you go into a company and teach the staff. Also, as I mentioned, speaking at industry events. All of these activities help your career and can be remunerative and enjoyable.

Let’s say you’ve done an assignment for a company and the project is successful. The client might say, “How much would you charge to come to our offices and show the marketing staff how to do this?” That’s a good signal that the market is ready for you — and vice-versa.

Doing this offers you lots of benefits. It’s egoboosting; it gets you out of the house; you meet people; you learn new ideas that can be recycled into your writing.

I understand that some writers are reclusive. Maybe that’s why they chose this career. I was that way myself. My ex-wife said I never had to leave the apartment because, before fax and email, Federal Express would pick up my copy and deliver new assignments. I subsequently discovered that it was enormously enjoyable and rewarding to get out there and share what I know about marketing and copywriting. And to hear audiences tell you how valuable your advice was, to flood you with compliments and questions. Especially in a public forum such as a professional conference, the celebrity and adulation can make you feel a bit like a rock star!

Can you share any lessons about growing a freelance business?

I never made cold calls. As I said at the outset, referrals are the best way, preferably from existing satisfied clients. But that doesn’t always take you far enough, especially early on.

So the second best method is what I call the “public relations” techniques. This means writing and speaking to your target audience. I’ve already talked a bit about speaking, so I’ll focus here on writing for self-promotional purposes.

Today, the emphasis is on social networking and blogs and video and so on. But for most of my career, there were print publications that were required reading for my clientele. Because I specialized in information products, I wrote for publications that were read by periodical publishers. I never had a shortage of topics. I wrote about how to solve the problem of people claiming to have too much to read, how to make copy credible, how to use human interest to make a promotion more powerful.

These publications usually didn’t pay much, or anything. So I requested that the article include my photo, a brief biography, contact information, and sometimes a note: “If you want a report on this subject, contact Don and he’ll send it to you without charge.” Readers contacted me and some became clients. I also reprinted these articles and distributed them as publicity pieces.

It’s synergistic. I always asked: “How did you find me?” The answer: “I read your article” or “I heard you speak.” And sometimes: “I read your article and then I heard you speak.”

Where can freelancers find worthwhile speaking opportunities?

In a word: everywhere. Every professional field has its seminars, conferences, annual conventions, breakfast and lunch groups that meet weekly or monthly. Sometimes the organizers are desperate for qualified speakers. I never found it difficult to get bookings. You have a rapt, captive audience consisting of people who might hire you. As with writing, you’re not paid big fees. You might get a small honorarium, or expenses if you’re traveling to another city. But the rewards are the exposure, generating new business, building your reputation.

Do you have any final advice for aspiring writers?

Over the years, I did a lot of corporate training. Now that I’m retired, as mentioned, I do pro bono consulting for causes I advocate, such as think tanks and other small charitable institutions. I help them with fundraising. Because of time constraints, though, I prefer not to write the copy. Instead, I say: “You take a crack at it, then I’ll review the draft and help improve and polish it.” Let’s say it’s a direct-mail fundraising letter. I’ll do some editing and explain how to fix the problems.

Now, here’s the point: I had this naïve idea that my “students” would absorb these lessons and do it right the next time.

And that didn’t happen?

No. Not usually. Some folks did learn. But I was shocked when many of these people sought my help later on, and they were making the same mistakes all over again! And they’re educated and intelligent.

This had me mystified. Finally, I asked one of them point-blank why it was happening. The answer: “Don, you do this all the time. It’s very tough for someone who isn’t a professional copywriter.”

So the moral here, which is encouraging for us, is that skilled copywriters will always be in demand because most business owners and nonprofit staffers just don’t possess the knowledge or skills or time or desire to do it themselves. The talent to sell with words is rare. And if you position yourself properly, and pitch your services correctly, people will be willing to pay for that capability.

This interview was previously published in the September, 2013 issue of Barefoot Writer. To read more interviews from fellow Barefoot Writers be sure to check out The Barefoot Writer's Club.

The Barefoot Writer

The Barefoot Writer

Discover a lucrative style of writing that will give you as much freedom as you can have while earning a great income at the same time. Learn More »


Click to Rate:
No ratings yet
Published: April 30, 2018

Guest, Add a Comment
Please Note: Your comments will be seen by all visitors.

You are commenting as a guest. If you’re an AWAI Member, Login to myAWAI for easier commenting, email alerts, and more!

(If you don’t yet have an AWAI Member account, you can create one for free.)


This name will appear next to your comment.


Your email is required but will not be displayed.


Text only. Your comment may be trimmed if it exceeds 500 characters.

Type the Shadowed Word
Too hard to read? See a new image | Listen to the letters


Hint: The letters above appear as shadows and spell a real word. If you have trouble reading it, you can use the links to view a new image or listen to the letters being spoken.

(*all fields required)