TCC Podcast #84: The Dark (and Light) Side of Freelancing with Steve Roller

Copywriter, author and copy coach Steve Roller stops by our studio for the 84th episode of The Copywriter Club Podcast. Steve is the founder of The Copywriter Cafe Facebook group—a group that a lot of club members are also in. We asked Steve to share his thoughts about his book, the field of copywriting and a whole lot more. Here’s what this episode covers: •  how a 17-year career in sales (and an online course) led to his second life as a copywriter •  how he connected with his first client (it involved pancakes) •  the advice he gives copywriters who are struggling to gain traction •  the advantage copywriters with a sales background have over other writers •  what it takes to foster engagement in a Facebook community •  the importance of relationships for all (but especially new) copywriters •  the books he recommends to copywriters who are just starting out •  the skills you need to be good at on client calls •  why every copywriter needs to write their own book •  how writing a book has affected his business •  the dark side of freelancing (spoiler: you won’t make millions working at the beach) •  the lighter side of freelancing—it’s definitely not all bad •  what Steve sees happening with copywriting in the future This was a great conversation with someone who is doing a lot to support other copywriters and help them succeed. It’s no wonder we feel such a kinship with Steve. You can get this interview on iTunes, Stitcher or by scrolling down to click the play button. Or you can read the transcript if you scroll down the page a bit.   The people and stuff we mentioned on the show: The Copywriter Café Never Eat Alone by Keith Ferazzi How to Win Friends and Influence People by Dale Carnegie The Freelancer Manifesto by Steve Roller Death of a Salesman by Arthur Miller Cafewriter.com Kira’s website Rob’s website The Copywriter Club Facebook Group Intro: Content (for now) Outro: Gravity   Full Transcript: This podcast is brought to you by The Copywriter Think Tank, our mastermind group for writers who are serious about taking their businesses to the next level. In the Think Tank, you’ll learn from guest experts who share their business and copywriting expertise; you’ll have the opportunity to sit in the hot seat while the other members of the group brainstorm solutions to the challenges you’re facing; and, you’ll have exclusive access to a small, focus group of professional copywriters who are all working together to get better at what we do. It’s not cheap, but it’s worth the investment. If you’re interested in learning more, visit www.copywriterthinktank.com. Kira: What if you could hang out with seriously talented copywriters and other experts, ask them about their successes and failures, their work processes and their habits, then steal an idea or two to inspire your own work? That’s what Rob and I do every week at The Copywriter Club Podcast. Rob: You’re invited to join the club for episode 84 as we chat with freelance copywriter, author, and community leader Steve Roller about the dark side of freelancing; the skills you need to make it as a consulting copywriter; why you must ride a book; and the impact a great community can have on your career. Kira: Welcome, Steve! Rob: Yeah, welcome Steve! Steve: Hey! Thank you very much for having me; I’m honored to be here, and excited to talk to you today and share some ideas with your readers. With your readers...I’m thinking ‘book’ already! With your lis— Kira: They’re going to be readers! Steve: Laughs Rob: Readers, listeners, yeah. Steve: With your listeners! No, I’m excited to be here. Thanks for having me. Rob: We’re really grateful that you are taking the time to talk to us. You’ve been on our list for a little while. We’ve sort of watched what you’ve done in your community and with your book and so, we’re just really excited to just kick off this conversation. Steve: Excellent, excellent. Thank you. Kira: So Steve, let’s start with your story. How did you end up as a copywriter? Steve: Yeah, so before I ever heard about copywriting, I was in sales. So, my career coming out of college and for seventeen years, actually before I did this, was in direct sales. So I worked for a couple of different publishing companies. And, I loved it. I loved the whole sales world, I loved the autonomy of working for a company but kind of being on my own. I was pretty good at it so I made good money. I went on some nice trips and got recognition and all that kind of stuff. But the only drawback for me was that I only got like three to four weeks of vacation every year, and I really like traveling and taking extended vacations and what I call Sabbaticals. That wasn’t enough for my tastes, so, I was looking for something to do to get out on my own, and this was like back at the end of the 90’s. And this goes back a few years, so back at the end of the 90’s, you know, when everyone was getting into dot-com businesses and stuff; I was really intrigued by that whole world but didn’t know what to make of it, and it wasn’t until about five years later, 2004, I was just surfing the internet and I came across an ad online for a copywriting course, a really great copywriting course, and it just really intrigued me. I had never heard the word; I had never heard of the concept, even though I was in sales and knew a little bit about marketing, I just never heard about copywriting, so I bought the course. I dove into it you know, I just—I really just fell in love with the whole concept of copywriting, and decided that someway, somehow, that was what I was going to do. Well, it took about four or five years before I was able to really make the transition into full-time copywriting. But anyways, that’s kind of how I got my start. So I found out about it online and took a course, and kind of did it on my own for two years and actually really didn’t do much for a few years. Chuckled; I took courses; I soaked it up; I read books, but I didn’t really have any clients for a few years actually. Rob: So how did you find those first few clients that came along? What were you doing to reach out and connect with them? Steve: Well, I really wasn’t doing anything but, I went to a conference. I went to a copywriting conference, and that’s when I decided, “Okay, I’m going to make a go at this.” I was still working a full-time job, and when I got back, about a week later, an old friend of mine from college invited me to breakfast. He was in town, and he said, “Hey, let’s go to breakfast,” and we caught up with things and he asked me what I was doing, and this was the first time I ever said, verbally, “I’m a copywriter.” I had never uttered those words before, and I really didn’t feel like a copywriter yet because I didn’t have any clients, but I told him I was a copywriter. And he said, “Oh, that’s interesting, because we just fired our copywriter.” Happens to be that he was the president and founder of a sales training company located in Madison, Wisconsin where I lived, and so he said, “Hey, why don’t you come to our weekly meeting next week, and just, we can talk, you know?” So I thought we were just going to have a casual chat; well I showed up at their weekly meeting, and I was the featured guest that day. And uh...laughs...I was a little unprepared. But he said, “Hey!” He introduced me to his whole team of ten people, and he said, “Hey, Steve is going to give us some copywriting and marketing ideas. So Steve, take it away!” Laughs. Rob: Surprise! I like it. Steve: So that was my baptism by fire into copywriting! So I kind of winged it; I knew enough from reading books and having gone to this conference. I knew enough that I could kind of talk my way through it. And then, I proceeded for the next six months do some work for them, so they were my first client. And I didn’t have a website, didn’t have a business, and didn’t really know what I was doing but, he gave me a chance, and I delivered, and from there I really just talked to a lot of local clients. I didn’t have a website for about a year; I didn’t know anything about how to market myself, but I just told people that I knew that I was a copywriter, so, another buddy of mine who was the president of an insurance company, another guy who was a personal trainer, another guy who owned a coffee shop, so you know...my clients were just this random assortment of people, but it was all people who I knew, and who knew me, and they trusted me, even though I had no credentials. Laughs. Kira: What advice, Steve, do you give to new copywriters, like yourself back then, who are really struggling to get those first few clients to gain that traction early on? What would you tell them? Steve: You know, I do tell people all the time to talk to people that you know. I mean, everybody has problems. I think the tendency is to gravitate—and there’s nothing wrong with this—the tendency is to gravitate toward big companies and the big publishing, the big Agora-type companies that everybody would love to land as a client, but as a beginner, the chances of landing those kind of clients are slim, but, I always tell people, there’s business everywhere, you know, in our own backyard, and I think we overlook that sometimes, but talk to people you know. Talk to people in your local community. Talk to people who have businesses. And, everybody has problems. They may not even know what copywriters are, or what copywriters do, or they may never have hired copywriters, but every business has problems. So I tell new people to focus less on their copywriting aspect of it, and just focus on, “Hey, what problems do you have as a business? Do you have problems... Would you like to bring more leads or keep more clients that you have? You know, how’s your advertising going?” You know, and talk in terms that people understand,