Introducing: Steve Roller, copywriter and marketing guy

Emida and I in Buenos Aires for our 10th anniversary, April 2008

Emida and I in Buenos Aires for our 10th anniversary, April 2008

Once a month, I take a brief detour from web copywriting, direct response and marketing advice, and give you a glimpse into my personal life.


Well, a lot of my clients and prospective clients have never met me in person.  Some would prefer to keep it that way, but others want to know more.

They want to know a little more about the person behind the keyboard, cranking out web copy and print materials that sell.

Why I’m a copywriter

In July of 2004, three big loves of my life (besides my wife and four kids) converged to create the career I had been waiting for.

I love to write, I love to sell, and I love to travel, and each one plays a part in my life as a copywriter.

Steve Roller, writer

I’ve loved writing ever since my 4th grade teacher (Ms. Biwer, if you’re out there – thank you!) pulled me out of class to compliment me on my writing journal.

Later, it continued with a travel journal as I backpacked across Europe in my early 20’s.

Most recently, it popped up as I started my first book, an inspirational biography of sorts.  The Great American novel is still rolling around in my head, while I pursue my copywriting passion.

Steve Roller, salesperson

Copywriting is selling with words, online or in print.  You simply have to know how to sell to be an effective copywriter.

Thankfully, I learned how to sell long before becoming a copywriter.  You could call it a baptism by fire!

In the summer of 1986, after my freshman year at UW-Madison, I had the wonderfully crazy job of selling educational books door-to-door, 81 hours a week, on straight commission, 1500 miles from home.

You can’t help but learn how to sell in that situation.  You learn how to read people quickly, how to figure out their wants and needs and hopes and fears, and how to quickly grab their attention.

You learn what motivates people to buy, and you expertly lead them to that decision.

Over the next five years I mastered the art of selling.   I loved the feeling of improving people’s lives because our paths crossed and I communicated effectively.

I’m still selling everyday with the words I craft, and I still get stoked about a successful campaign that brings in a lot of new customers.

Steve Roller, traveler

Selling skills and writing skills (and a love of those things) make sense for a successful copywriter.  But traveling?

Let me explain.

My career has mostly been in direct sales.  I’ve sold educational books door-to-door in 5 different states back East.  I’ve sold legal publications to high-powered attorneys in Minneapolis.  And I’ve been in fundraising sales, helping schools and non-profit organizations in the Madison, Wisconsin, area raise well over $1 million in profits.

Great jobs, all of them.  But they all required me to physically be there in person, making presentations face-to-face (I figure I’ve made over 25,000 such sales presentations.)  If I wasn’t on selling appointments, I wasn’t making money.

My wanderlust is too strong to be physically confined to one place.

When I found out I could use writing and selling skills as a copywriter, and indulge my passion for traveling at the same time, I leapt at the chance!

Copywriting freedom

Most recently, I spent 17 days in Istanbul, Turkey, and Lagos and Benin City, Nigeria.  As a copywriter, my “office” was under the coconut palms and avocado trees, soaking up the 90 degree sunshine.  I spent 17 days relaxing, writing a few hours a day, and making money while I was on vacation.

I’ve been to all 50 states, 30 countries, and 5 continents so far.  I have big travel plans for the future, and they all involve copywriting on the move!

Writing, selling, and traveling.  A melding of three of my favorite things into my perfect career – copywriting.  And being a copywriter gives me flexibility and time to spend with my two great loves – my wife and kids.

That’s what really counts.

Steve Roller

Author Steve Roller

I'm a business coach, author, copywriter, world traveler (33 countries on five continents so far), and professional speaker. In addition to helping companies get more customers and make more money, I help other writers create profitable businesses. I offer one-on-one coaching, professional copy critiques, and live, in-person business-building workshops. When I'm not writing, coaching, or speaking, I enjoy nothing more than hanging out with my wife and four kids and planning my next adventure.

More posts by Steve Roller

Join the discussion 16 Comments

  • Tanya MarCia says:

    You inspire me!

  • Joel Childers says:


    Congrats on your success! I am a member of AWAI and much like you are still wondering if ‘this copywriting thing” is possible. But it seems as though it is by your own personal testimony.

  • Massive Steve! Thank you so much for being in all of our lives!

  • John Rugh says:

    Steve, thanks for the inspiration and all the great things you do for the Copywriter Cafe community!

  • KIGOZI ALEX says:

    I see my self in you but the feelings I have at the moment propel me to think that such projects can only be achieved by the people who are in America not Africa where I live.Not so many people or companies here can hire the skills like you have.I am not complaining but is the gospel truth that such entities have not found real value in writers.A lot can be done if you come out to tell me how I can do it in the areas you done without to much ado.

    • Steve Roller says:

      Njaleruma – thanks for your comments. I agree, there probably aren’t as many people in Uganda as in the U.S. that will hire someone with these skills. Still, if you want to be a successful copywriter, you can operate online and offer your services all over the world. The key is getting good as a copywriter, because you’ll also be competing with people all over the world online.

      If you truly desire to do this, I would say study the art of copywriting diligently, and practice, practice, practice. There are many good free online resources, including websites like and this one. That can get you started, as well as searching “free copywriting training.”

      Best wishes, and let me know if I can help you with more advice.

  • Mark says:

    I am…again…inspired. For the past couple weeks, I’ve been exploring where I went wrong with my copy writing business. I’ve had a few key insights, but one was in your post today, and it hit me like a ton of bricks…SELLING.

    I caught myself saying to someone recently that I’m not very good at selling. The next thought was “why should I waste my time copywriting?” But then I turned it into “I need to learn how to sell to be an effective copywriter.” So if I take care of this, along with the other key things, like building a business, I think I’ll finally get it right.

    Thanks again Steve.

    • Steve Roller says:

      You’re welcome, Mark. I’m realizing this is a challenge for a lot of copywriters, and I plan to address it soon with a simple program. I’ll keep you posted.

      In the meantime, if there’s ever anything I can do to help you, let me know.

  • Jen says:

    Love it Steve! It’s pretty amazing that we live in a world where we really can create our dream lives 🙂

  • Hey Steve, you weren’t born in October, were you? Cuz from this post, I see that we do have a lot in common. And if you were born in the month of October, or your zodiac sign happen to be Libra, that would just seal the deal.

    By the way, rising early is never where you’d find me hanging….

    great post sir.

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