Steve Roller is a direct response copywriter, world traveler (30 countries and five continents so far), marketing strategist, and professional speaker. He is also a personal trainer to aspiring copywriting rock stars. Steve offers one-on-one and group training, professional copy critiques, and the Ultimate Writing Retreat™.
He also has created a great Facebook community, Copywriter Café, where writers from all types of backgrounds gather to gain insight and encouragement for developing their craft.
Without further ado, here’s the interview:
When you were a little boy, what did you want to be when you grew up? Were you always a writer?
Up until the age of 15, I thought I was going to be a major league baseball player. I was a little delusional, because I wasn’t that good.
When I finally figured out in high school that baseball wasn’t in my future, I gravitated toward math and science because I was pretty good at both. I went to school at the University of Wisconsin – Madison, planning to major in chemical engineering. Three semesters in, I realized I was in over my head and transferred to the school of Letters and Science, majoring in Economics.
I never considered myself a writer, but two instances from my school days stand out very vividly now, even 30+ years later. One was in 4th grade when my teacher, Ms. Biwer, pulled me outside of class to compliment me on my journal writing. The other was my senior year of high school, when my Psychology teacher, Mr. Lewis, bragged on me in front of the whole class about what a great job I did on an autobiographical writing project.
Things came full circle last summer when Mr. Lewis contacted me and asked me to edit and proof his second novel.
If you weren’t always a writer, how did it develop?
After college I went into direct sales, first for a legal publishing company and then for a school fundraising company. During this time I created a lot of my own prospecting and follow-up sales letters, without having any clue what I was doing. It came naturally, and I developed a “conversational writing” style that I still have to this day.
Two other small things contributed to my writing experience, too, if you can call it that. I was the secretary for my Toastmasters group for a couple years, and members loved the way I wrote up the meeting notes (a bit more entertaining than the previous secretary’s dry reporting of what happened).
Also, every year I sent out a lengthy letter with my Christmas cards, re-capping the year with fun stories and interesting anecdotes. One year when I didn’t have time to do it a bunch of people asked me where it was and when it was coming. People really enjoyed it.
So that’s the sum total of my writing experience. Oh, and maybe two college essays in four and a half years, neither of which were very good.
Did you write for any of your jobs before launching your own freelance business? When did you launch your writing business, by the way?
Only writing I did was sales correspondence, as indicated above.
Once I discovered copywriting, I dabbled in it for a few years without really applying it. I studied it and knew a lot, but didn’t have any practice, no clients.
I finally got serious in October of 2008, got my very first client in early November, which turned into a regular monthly gig for about six months, and launched my full-time freelance business on March 30, 2009. “Full-time” is a bit misleading, however. I didn’t have a whole lot of business that first year. By the second year, I was making a decent amount.
What are some of the things you know now that you wished you knew when you first started?
- Your skill at copywriting is important, but your marketing skills and willingness to promote yourself are much more important.
- No one besides maybe your spouse cares if you succeed or not. Friends may wish you well, but ultimately it’s completely up to you to do it. People love talking about “firing their boss,” but you know what? Bosses or managers are great because they tell you what to do, when to do it, and hold you accountable!
- Clients don’t care too much about your experience. They’re mostly concerned with the results you’re going to get for them.
- People will hire you because they like you, and if they think you can get the job done. Stretch yourself and go after jobs before you think you can easily do them.
- Get help. Get a coach, a mentor, someone to guide you and help you. Being a “lone wolf” is very, very tough in this business. Ask for help.
- Paying all your own expenses, insurance, and self-employment tax is not fun.
I have a bunch more, but one more …
- “The writer’s life” is not everything it’s cracked up to be. Yes, I absolutely love it now and wouldn’t trade what I’m doing. But the first few years are hard, you probably won’t get rich, you won’t be working two hours a day on the beach with your laptop making a full-time-style income, and clients won’t beat a path to your door just because you finished some course and hung out your shingle!
There, I’m done ranting, for now.
How did you find clients? (Always a favorite topic for freelancers!)
I always tell new freelancers, start with who you know and what you know. What you know meaning start with topics and areas that you maybe know something about and are interested in.
I got my first two jobs from personal friends from back in college, who now had their own businesses. One came about over breakfast while catching up on things. The other one got my Christmas letter and contacted me.
From there, I got local clients through good old fashioned networking and referrals, and my business started growing. I also made a key connection at AWAI, Katie Yeakle, and she hired me to do some small projects. They turned out well, and I’ve been writing for them consistently ever since. I owe Katie a debt of gratitude for giving me a shot, and for referring other business my way.
I know that you travel extensively. What is it you love about traveling?
I love exploring off-the-beaten-track places. I love new experiences and people, and the challenge that comes with international travel especially.
I got the travel bug hard when I took a semester off in college and backpacked all over Europe for three months. On a whim we took off for Egypt and spent two weeks there, too, and it was the adventure of a lifetime.
Since then I’ve traveled to all 50 states and Puerto Rico, and I’ve been to 30 countries on five continents. I once hit four different continents in a 48-hour period (a story for another day).
What are some of the traits you think are valuable to have for a writer/freelancer?
Initiative. The ability to get started without someone telling you what to do.
Drive. You have to be hungry to do well. If you’re content with being average, there are much easier ways to do it.
The ability to read people and really understand them. You have to be able to get inside the heads of your readers, and figure out what makes them tick … what their hopes, fears, frustrations, and aspirations are.
Curiosity. You have to be naturally curious about people and the world around you.
Imaginative. If you can generate fresh ideas on a regular basis, you’ll be in demand.
And finally, I’d say it helps to have the skill of being able to make connections. By that I mean being able to observe the world around you, understand people, determine what they really desire, and make a connection through your writing between what they want and what you have to offer …
… all done in a smooth, compelling, persuasive way (another skill, of course, which can be learned).
Why did you start your writing retreats?
I started the writing retreats mainly for selfish reasons! Seriously. I love traveling, as I mentioned, and I love getting together with small groups of really interesting, creative people, hanging out and discussing lofty ideas, and then connecting those ideas into well thought-out business plans.
I also saw a gap in the marketplace that wasn’t being served. Big conferences are great for listening, taking a ton of notes, and doing some networking.
But there’s something really special, magical, about small groups of maybe 8-15 people coming together, brainstorming, learning, creating, and generating some serious big ideas.
All things that wouldn’t happen without getting away from it all in unique settings like the ones I choose for my retreats. The feedback from the three retreats I did in 2013 was phenomenal, and I’m doing three more in 2014, with plans to expand even more the following year.
What question do you wish I asked that you’d like to really answer? :-)
“What do you want to be known for, Steve? What legacy do you want to leave?”
I’m glad you asked, Mary Rose! Thanks. When I come to the end of my life, I want people to think, “You know, he really made an impact on my life. I wouldn’t have done the things I did if it wasn’t for Steve’s influence in my life.”
I have big plans to help at least 1,000 people over the next ten years develop a solid full-time income from their copywriting and marketing skills. Not necessarily to become a freelance copywriter per se, but to use writing skills, big-idea thinking, and effective marketing systems (all things we work on at retreats and in my personal training sessions) to build a business. A true, income-producing, valuable asset.
Oh, and I also want to become a world-renowned author and speaker. That’s all.
Thanks so much, Steve, for a great interview! And I have a feeling that if someone wants to meet you, no matter what part of the world they’re in, it will be possible given your itinerary!