TCC Podcast #84: The Dark (and Light) Side of Freelancing with Steve Roller - The Copywriter Club
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
Kira’s website
Rob’s website
The Copywriter Club Facebook Group
Intro: Content (for now)
Outro: Gravity


Full Transcript:

Copywriter-Steve-RollerThis 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

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, and talk about solving problems and giving people ideas rather than, “Hey, I’m a copywriter; do you need any copywriting work done?”

Kira: Yeah that’s such a great reminder, because I think it’s really easy—especially with the only space, for new copywriters to just focus on landing online businesses, but they’re so many local businesses and local people. If you step away from your laptop and actually approach people and join local organizations, maybe that is a better approach early on.

Steve: Yeah, yeah. For sure. So, lot of different ways and you know, these days there’s all kinds of ways to market yourself online and join in groups, and networking online and stuff like that. But I think that’s one way that people, for a beginner, it’s an easy entry into the copywriting world.

Rob: So Steve, I want to back up just a little bit. I think that you had a pretty extensive background in direct sales, and as I think about some of the copywriters that we’ve talked to or heard from, that seems to be relatively common, that a lot of people come from that area into copywriting. Would you say that there’s particular skills that you learn in that industry that made you more likely to become a copywriter, or have helped you as you launched your business, and really grown into what it is today that you got from those days in direct selling?

Steve: Yes. First of all, I’m actually kind of surprised that more good sales people don’t transition into copywriting. You’re right that a lot of great copywriters do have a background in direct sales. For me, I think there’s a couple of qualities; and there’s two parts to this answer, maybe. One is that I think high-performing copywriters have, and this is true for highly-performing sales people, is that you have drive and their motivated by money, and they like getting things done, and they like results. But, mostly it’s just the fact that if you have a background in sales, and then you transition into copywriting, you truly understand selling, from a standpoint that copywriters who haven’t sold don’t get on that same level, you know? It’s the psychology of the one-to-one selling, which is really what our copy should sound like, you know, or always striving to sound like we’re talking, you know, one-to-one, like, to one person. Well, you’ve been in sales and you’ve sat down across the table or you’ve been on the phone with people and you’ve done a lot of selling, you really understand that one-to-one selling and the psychology of selling. So I think, you know, copywriting is a learned skill just like selling is a learned skill, but if you’ve done it a lot, it’s just more…like now, when I talk to clients on the phone for the first time, it’s just…it’s a natural instinct for me to understand how to lead them through the conversation, and to establish rapport and have a little bit of an introduction and pull them through my presentation, just like we do on paper with copy, but a lot of copywriters don’t get that part of it, the phone-selling and the talking and the face-to-face selling that we still have to do as copywriters with clients. So, I don’t know if that answers your question, Rob. But I think it’s just good, you know, people who have a sales background, understand this psychology of selling at a deeper level than most copywriters do.

Rob: Yeah I think it’s a great skill to have. Maybe not absolutely required to start out with, but, at some point you need to develop it.

Steve: Yeah, for sure.

Kira: So for anyone listening who’s not familiar with you or your community, can we fast-forward from your story of how you started and those first few clients, and talking about where you are today, what you’ve built over the last however many years, and what your business looks like today?

Steve: Yeah. So as a mentioned, I found out about this whole thing 2004; and 2009–so it’s been exactly nine years ago this month—that I jumped into it full-time, freelance copywriting. For the first few years, 2009, ‘10, ‘11, i was just, you know, writing for clients, just taking any kind of business that I could get. And just, really diving into it and just trying to get my schedule full. At a certain point, I was doing some writing for another organization who markets themselves to copywriters, and so a lot of people were seeing my name online and in articles, and blogs and stuff like that.

So, little by little, other copywriters started just asking me for advice; so they were asking me, you know, just how to get started, how to get clients, things like that. Sometimes out of the blue, I would get a phone call back when—heh—back when people used to pick up the phone and actually call people. Out of the blue. So, I’d occasionally get phone calls and people would say, “Hey Steve, I saw your name on this article, and you know, can you tell me about this, and…” So, I realized that there was a need for people beyond the courses and the big marketing companies that well selling programs to copywriters and I realized that people were still really hungry and needing information about how to get start and stuff, so, 2012, I started this Facebook group called The Copywriter Cafe, so I thought well, people are asking me for advice, maybe I’ll just start a little group. And I had no plans for it; I didn’t have any intentions of monetizing it, or, you know, I just thought hey, let’s have a little group together here, and contacted about thirty or forty or my friends who were copywriters that I’d gotten to know. And we started this little group called The Copywriter Cafe, and it was just kind of a virtual hangout. It was a place to, you know, kind of encourage each other and help each other, and give advice, and get ideas and just, you know, it was just a very casual kind of thing.

And, just over the last, you know, five-and-a-half years know that I’ve been doing that, it’s just—it’s growing, and it’s grown from, you know, thirty or forty people to, I don’t know, seventy-nine, a hundred or something like that now. And I know, it’s just like, you guys have a Facebook group that’s grown quite big too. it’s just, there’s a need for people to hangout online, so that’s kind of where I am now, and that takes up a bulk of my time now, just kind of overseeing this group and this community.

Rob: Yeah, that sounds familiar, the whole “bulk of your time going into a community”.

Steve: Laughs.

Rob: There’s a lot that it takes that foster and grow a community that’s engaging and as a member of your community, I admire a lot of the things that you guys do, you know the engagement you have. Can we talk a little bit about that? What does it take to create? Because there are some really copywriting groups out there, and there’s some that are dead—you know, no engagement—and you know, I’d like to think that ours is real similar to yours in that it’s a positive vibe, it’s helpful… What does it take to help foster that kind of a community?

Steve: Well, number one, I mean, just, as you know with your group, that it takes a lot of involvement, a lot of time, and a lot of time on your part as the founders and the administrators, but it’s a team effort, and I think just cultivating that vibe of—and it’s been intentional on my part, you know, because I see what else is out there, and I’m aware of the other groups, and the vibe of some of the other ones, but in our group, we’ve just really tried really hard. This is through my posts, and the way I interact with people. Really try to cultivate just, more of a friendly, upbeat vibe, and we’re also very patient with newcomers.

Sometimes people feel intimidated in certain groups because there’s a lot of expert level, professional level people, and we have a wide variety of in our group. We have twenty and thirty-year pros, but we have lot of intermediates, but we have a lot of beginners too, and, you know, we don’t mind the questions like, “Hey, how do you get your first client?” and “How do you build a portfolio?” and this kind of stuff. So yeah, we’re patient with people, and we’re accepting of everybody but, I guess it just takes a lot of work; it takes a lot of time and, for me, I guess the other thing is just—and this is just the beauty of the community, is—the building of relationships.

So, I try and what people don’t see behind the scenes is there’s a lot of interaction and relationships and, you know, conversations going on behind the scenes too, so, out of this big group that I have, I’ve probably had conversations, like phone or Skype conversations, with I don’t know, maybe five hundred, a thousand people? I’ve probably met in person three or four hundred of them. I’ve done events, and I’ve had a hundred and fifty people at my different events. So you know, we know each other offline too, then wherever I go too, and this, this is the other part, you know you’ve got a virtual group and it’s a great thing that people all around the world and all around the country and come together in this virtual space. But, I also try to meet up and do casual—I call them “Cafe Meetups”—whenever I’m traveling, so, like, just this last weekend I was down in Atlanta, and we had a little small Cafe Meetup with some people in the cafe down in Atlanta. Last time I was in New York City, I met with a few people out there. When I’m in L.A., I, you know, meet with a few people out there. And even as far as going to other countries, when I’m down in Ecuador, I’ve met up with people from the Cafe in Ecuador! So that’s kind of cool. So, we know each other and we like each other, and it’s a fun group, and I genuinely like…not everybody, but I like most—

Kira: Laughs.

Rob: Laughs.

Steve: You know, I’m not going to go that far! But…

Kira: Thanks for being honest!

Rob: Well I am in the group, right?

Steve: Laughs. I love you guys, but you know. But I do, I….you know, I would say a lot of my really good friends who have developed into good friends are my friends and people in the Cafe, and that’s a cool thing. I didn’t set up for that to happen, and I didn’t know it would happen, but it’s just a nice, natural byproduct. So it’s kind of cool.

Kira: I’m always looking for new friends, so i think that’s part of why I’m so excited about building this community with Rob. You know, clearly relationships are important to you, to us, with community building, but I feel like relationships are also really critical to the success to any copywriter, especially new copywriters. Maybe even more so than we think.

Steve: Yeah.

Kira: Can you just speak to that for a bit? I think it’s easy for us to just get locked into training after training without actually building relationships.

Steve: Yeah, that’s a great point Kira. And, I would say that, you know, there’s one thing that I built my career on, it isn’t that I’m the best copywriter, because that’s not true by any means. I’m a good copywriter, but not great. It isn’t because I’m great at marketing, because I have particularly done that really well either, but really, it’s building relationships, and I think that is one thing new copywriters can do. So they’re not going to—a new copywriter coming out of the gate is not going to be able to compete with a seasoned pro and somebody who’s really good at marketing, and really good at social media and all this stuff, but anybody can develop authentic relationships. And I tell people all the time—I tell copywriters all the time—you don’t have to have tons of clients. You know, people are kind of surprised when I tell them in my whole copywriter career, I’ve had less than a hundred clients.

You know, people are like going, “What? How did you—how have you made any money with less than a hundred clients?” Well, it’s because a lot of the clients that I’ve had have stuck with me. I’ve got a client that I’ve been working with for eight years straight now, monthly retainer client that I’ve worked with for eight years straight. I had another client that I worked with for over four years, and that’s been the case with a number of people but, not only just clients, but developing relationships with other copywriters, with marketers, with people who have complimentary services to you and getting referral businesses from those people, but yeah. That is probably one of the biggest things that I focus on, is the importance of connecting, and that’s something I talk about in my book, just the skill of connecting. And it really is a skill. I mean, two books that I always recommend to people, if they want to get book at this skill of connecting, and really just let this whole idea sink in and really immerse yourself in it, one book is Never Eat Alone by Keith Ferrazzi. Have you guys read that book at all.

Rob: Yes, great book.

Kira: I’ve heard of it.

Steve: It’s a great book. I heard him speak a few years ago, and I was—actually, to this day, he’s probably the most impressive speaker I’ve ever seen on stage. It was just unbelievable. But his book Never Eat Alone is a fantastic book about making connections, developing relationships, and that part of things, which I think we have the opportunity to do that more than ever now with where social media is and where everything is online, but I think people forget that. Another book is an old classic by Dale Carnegie that’s written back in 1935 or something: How to Win Friends and Influence People, and some people think it’s kind of a corny book and it’s outdated, and it’s kind of silly, but I still think it’s actually, there’s so many good core principles in that book and I just love, and I try to re-read it once a year, but those are two books that I recommend for people that really want to make sure that they’re emphasizing this relationship building.

Rob: Yeah, I’m glad that you mentioned creating relationships with other copywriters, because I’ve been surprised in my own business as I’ve build my own network with other copywriters as opposed to clients, how much business I’ve gotten from other copywriters, as opposed to, you know, having to go out and pitch new clients…

Steve: Yeah!

Rob: …the stuff just come because people know you, right?

Steve: Oh, totally. It’s just, it’s unbelievable, and it’s just funny, I don’t know—there’s a point, you know, in the beginning. You’re working so hard, you’re trying to get clients, you’re trying to get to know other people, but at a certain point, it just flips, and then things start coming to you, and they start landing in your lap, and sometimes I have trouble helping people with coming up with a good marketing plan because it’s been so long since I’ve done it, because it’s like—and this is hard, again, this is something that’s hard to teach but, on a weekly basis, things are landing in my lap, and I’m either taking them, or passing them off to somebody else, or helping them refer them to somebody else, but I mean, things—as you guys know from your careers too, you know—things just start coming to you. So yeah, Rob, totally. The importance of developing connections and relationships with other copywriters and, you know, because we can’t do everything, so we’re good at some things and other copywriters are good at other things, and everybody’s always needing people, so yeah. It’s definitely, definitely something people should do.

Kira: All right, so you’ve been in the game for a while; you’ve seen how the environment has changed for copywriters. What are some specific skills that freelancers need today in order to succeed, that maybe they didn’t need ten years ago?

Steve: Well yeah, Kira, things are definitely more competitive; things are moving much faster, you know, with trend and technology and the audience and the players, so… One is just constantly learning and being willing to adapt very quick to how business is being done. So for example, you know, when I started the idea of getting on a Skype call with a client, that is just a foreign thing, I just assumed everybody did it by phone. And the first time I did a Skype call, I’m like, “How do you…how does this work?” You know, so I mean, keeping up with technology now, I mean…things like just new tools and apps, and things constantly, so I think we’ve got to keep up on things. But, it’s also, as you know, it’s more competitive, and so the environment is changed. The great thing is the barrier to entry to get into this is low. That’s great, opportunity there for anybody that wants it. But, that also means that things are a lot more competitive, so I think you have to….this isn’t necessarily a hard skill, I don’t know how to describe this, but, you have to stand out somehow.

I think this kind of speaks to the idea of developing some kind of a personal brand somehow, and really making yourself stand out, so it’s not enough to just be, you know, a copywriter. I don’t think it’s even enough just to specialize in a particular subject niche, even. But, I think you’ve got to somehow stand out as a person, and really build your personal brand too, and that could be a whole other podcast. There’s people who talk about personal branding that are much more of experts on that topic, but I do think that’s one thing that people need. The other skill’s just, you know, and this is always going to be the case, so it’s not necessarily because of today’s world, but, obviously copywriting, the skill of copywriting, we need to always be working on that. But I think even more than that, going to back to what we talked about in the beginning, selling. Learning how to sell yourself and your ideas.

So, again, I’m not talking about selling on print with copywriting, but I’m talking about really getting good at the art of communicating what you are, and what you’re about; you’re ideas to your clients, like on client calls, and getting good at that part of things. And then, like we just talked about too, the skill of connecting, which I think is probably one of the most important skills you can develop. And that, the only way….sigh.

You know, and again, there’s not necessarily a book on this or a program, or you know, I mean those books I mentioned, but, I think it just takes practice. I think it just takes time and practice and experience of reaching out to people, connecting with people, getting good at figuring out, okay, not just how you can benefit from it, but, how can you serve other people. And I guess this would be a good approach, you know, for new people or anybody, but just going into it with, from the standpoint of, hey, how can I help you? What can I do? What can I do to serve you, and what… Is there anything I can do to serve you? And I say that to clients, I say that to copywriters all the time. And yeah, I’m looking for business, and yeah, I’m looking for ways to benefit myself, but truly first and foremost, I’m in this business to serve and I think if you go into it with that attitude, it’s all going to work out quite well.

Rob: So one of the ideas that I’ve heard you talking about lately, as far as building your own brand, is writing a book. In fact, I think you’ve said that every copywriter should have a book. Can you talk a little bit about that idea and why we all need our own book?

Steve: Yeah. Well, again, I think it’s to stand out. In one way, it’s to distinguish yourself from your competition. We all have a lot of competition, and so I think writing a book just helps you stand out. So I…I saw this a couple of years ago, in fact, I can’t remember the guy’s name now but, somebody in the Copywriter Cafe—probably in your group too, but—a guy that specializes in dental copywriting wrote a book about it. And it’s a paperback book, about 240 pages, and it’s got all kinds of great ideas, but I thought, you know what, I looked at it and it’s well-written and it’s great ideas and he’s writing it to his clients and saying, “Hey, here’s how you can do this, here’s how you can do this”, and it all, you know, feeds back to him and, you know, most people are going to read it and think, “Okay this is great, but we still need you to do it,” but I thought, “Hey, this concept—this concept of writing a book on his specialty—that could be taken for anybody, anybody that specializes in any particular niche or any particular service could write a book about that.

I recently got a paperback book that somebody wrote about how to do explainer videos, you know? So, it isn’t necessarily to sell a lot of books, but it’s to stand out in your field. And the other thing is it gives you instant authority. Everybody’s got a good website, you know, a lot of people have, you know, great social media presence, great marketing and all that, but writing a book is still the one thing I think that stands out above most. And it takes a little bit of time, and it takes some mental effort to put all your thoughts and ideas into cohesive way, that makes sense into a full book, you know? It’s one thing to write a special report of lead magnet or put some blog posts up, but, to put all your thoughts into a cohesive form of a book? That takes something, and it’s a daunting task that a lot of people are intimidated by, and a lot of people just don’t ever take the time to do. So, for that reason, if you do, it’s going to stand out. And, I guess above all too, it forces you to put your thoughts together in a way that makes sense, and once you do that, it makes it easier to convey those ideas to your clients. So, lot of good reasons, but I just think more than anything—and it’s just kind of an ego-thing, too—Laughs.

Rob: Laughs.

Steve: It’s kind of a cool thing to, you know, have somebody ask you to sign your book for them and stuff like that, and to see your name in print, and to have people buy your book and stuff, and…for me—chuckles—I think I talked about this in my group recently, but, I think my parents finally, after doing this for all these years, my parents finally realized, “Oh, Steve is a writer!” Laughs. They really understood what I do, and what an impact—my mom has been reading it. My hundred-year-old grandma…I gave a copy to my hundred-year-old grandma a couple of weeks ago, and I dedicated the book to her too. But, my grandma is reading my book and understanding! So, you know, she’s known me for my whole life, but she’s realizing things and understanding things that she never knew, and she’s fascinated by it! And, so, it’s just kind of a cool way to share your ideas with the world, in a way that other people might not get if you did it in other formats.

Kira: And what’s the impact been on your business? So I think there are a lot of good reasons you’ve shared already, and differently good reasons that your parents understand what you do everyday, but as far as the business purposes, did you have any clear goals attached to the book?

Steve: Yes, most definitely. Actually, that’s probably—I’m glad you said that Kira, because I’m like, okay, I’m telling all these other things, but yes. That is the real reason I wrote the book, is to drive people to my website, and to build my community. So I have my Facebook group, and I have a paid community too, you know, I did it sparingly in the book because I’ve read books where every other page is an advertise for, you know, “Go to this webpage”, or “Go to this site”, or “Buy this”, or “Do this”. So I was very careful with, you know, being…not overdoing it, but…yeah. I’m dropping URLs and links all over the book to drive people to my website. I want people to go to my website, get on my email list. So first and foremost, the purpose of the book was to build my email list, and the purpose of my email list is to build my paid community. So yeah, there’s most definitely a business purpose behind it. And I’m seeing that pay off already. I haven’t gone full-blown with the marketing for the book yet. It just came out a few months ago, but it’s already paying off in a lot of different ways, but it is driving people to my website, and I’m going to be going all-out on the marketing for the book in the near future here, too.

Rob: And that aspect of your book—when I was reading the book, I thought hey, this is very Dan Kennedy-esque.

Steve: Laughs.

Rob: Because that’s what Dan Kennedy does, you know?

Steve: Yeah, yeah.

Rob: He refers back to another program, or a different book or something. Yeah, you know, and I think it’s a really smart tactic to get people to engage with the things that you’re doing outside of the book.

Steve: Yeah. You know, people think, “Well, a book is old school.” Well, you know, and this is a Dan Kennedy concept too, Rob. But, you know the online-offline thing. You know, you have offline stuff to drive people to your website, and you have online stuff to get people to buy other stuff, you know, that’s physical. So I like being in both worlds, you know. Being in the physical real world with stuff, and obviously driving people to my website too.

Rob: So, also in the book, you talk a lot about the dark side of freelancing, and there’s some real negatives. I joked in an email to you that you’re destroying…

Steve: Laughs.

Rob: …my dream of working from the beach.

Steve: Laughs.

Rob: Can we talk a little bit about that? The promises that people, you know, hear around freelancing that just really aren’t true, or are only true for two or three people and the rest of us are going to suffer, you know, if we believe them. What is the dark side of freelancing?

Steve: Yeah, a good, good question, and I’m sorry to destroy your hopes of writing on the beach, Rob. Laughs.

Rob: Yeah, it’s…I’m done.

Steve: Actually, I have a feeling that, knowing you and your skills and where you are, I have no doubt that you could write anywhere you want to including the beach! But the whole thing with the dark side of freelancing… So, in my book, I talk about the dark side, and then I talk about the bright side, but what I’m referring to is this whole business of being a copywriter, being a freelancer in general, I think had been oversold. It has been made to sound too easy, too fun, too lucrative, you know? So we have courses and programs and events that promote, “Hey, you can make six figures your first year!” and “You can do this!” and all this stuff, and that’s certainly possible, but I don’t think people realize what that all involved, and how much work goes into this. And yes, it’s fun to be a freelancer, and be able to take off whenever you want, or work from wherever you want, and I do that and I bring my work with me whenever I travel.

But the dark side to me is the fact that, hey, this is not easy. You’re going to work really hard. It’s going to be competitive. You’re going to have expenses. You’re not just going to sit around in your pajamas all day and wait for things to come to you. You’re going to be paying your own expenses, you know, if you had a corporate job and you had insurance and benefits and all those things before, guess what? Now you’re going to be paying for those things yourself.

So, I put those things in the book first because I just want people to realize the reality of freelancing, but then I transition into saying, “Hey, okay. That is the dark side, and that’s reality, but if you’re still here; if you’re still reading; if you’re still in this; if you’re committed to doing this…. hey. Here’s some things that you can do to really make this work for you. And, funny story too, Rob, about the title of the book: so it’s called the Freelancer Manifesto, as you know: Eleven Big Ideas to Stand Out and Thrive in the New Economy. I had a really bad title to start with that somebody talked me out of, but I was so married to this idea. I was going to call it Death of a Freelancer, laughs.

Kira: Laughs.

Rob: Nice.

Steve: You know, that’s the play by Arthur Miller, Death of a Salesman; it was a play on that, of course. But somebody thankfully talked me out of that title. Laughs.

Kira: So, you mentioned earlier that part of the reason you wanted to start your own business was because you love to travel. And so, I guess to talk about the light side of freelancing, have you been able to travel since running your own business? I believe you have four kids, is that right?

Steve: Yes, so I have four kids, and now I have two boys that are in college, and…

Kira: Oh, wow…! Yeah.

Steve: …my two daughters are both in high school, so they’re grown up and almost all gone. But yeah, one of the big reasons I wanted to get into this copywriting was really to do my own thing. So, right after I started full-time copywriting, we were able to take a trip for the month of December that year to…my wife’s from Nigeria, so we were able to go back to Nigeria. I had actually never been to her home country. Never met her whole family, and we had been married for eleven years at that point, and I wouldn’t have been able to do that if it weren’t for being a copywriter, so we were able to do that.

And then, a couple of years later, we took the kids and went to Ecuador for four weeks, and then two weeks after that, we spend the entire Summer—the day after they got out of school in June—we left for Ecuador and stayed there for the entire summer. And I’ve done a lot of traveling, you know, just…I’d fly out to New York every few months, he’s in school out there and, just a lot of things like that. And then two years ago, I spent ten weeks—I’ve lived in Wisconsin, and it’s cold here in the Winter as you know, and I hate Winter and I hate the cold. So, two years ago, I spent the entire Winter down in Ecuador, and got out of Wisconsin for the Winter, so that was kind of cool. And again, all these things I would not be able to do if it were not for copywriting. But, for people that think I’m just lounging about and seeing the sites and being a tourist and stuff, that isn’t why I do it. It’s just to kind of get away and have a different change of scenery. But I bring my work with me; I’m usually working while I’m gone. So, to answer your question, Kira, it’s been great as far as being able to travel. And then, being able to do a lot of little trips and stuff with my kids, too.

Rob: One of the things I know you do, Steve, are some small-group, off-site type events, you know where you…you’re probably doing hot seat type business, ideas-generation things…Will you tell us a little bit about the kinds of topics that you talk with other writers in those kinds of events, and what you cover?

Steve: Yeah. So, I do these things called The Big Ideas retreat, and it’s a little bit different kind of event, then the bigger… Kind of three types of events: there’s the big events where you got, you know, few hundred people in a room, and all kinds of different speakers, those are great; you’ve got little bit smaller events where you’ve got maybe a small panel of speakers; well, mine are a little different too. We just bring in, like, usually ten to fifteen people. We go to a kind of remote location; I’ve done them up like in the north woods of Wisconsin; I do one in Vermont every year in the Fall, but they’re small and intimate. And, what people get at these events in hot seat, we do like a hot seat session where everybody gets an hour where we focus on them and their business, so you know, with me moderating, they kind of explain where they are in their business, what some of their challenges are, and then you know, going around the room with this small group, you know, everybody kind of offers ideas and suggestions and, I’ve had numerous people that have been in my events, to these retreats.

But that one session, that one hot seat session alone, was worth the cost and the time of coming to the event. But other than that, we work on a lot about, you know, the personal branding aspect of it, of building a business. And, more than anything, I think people just get a validation of bigger ideas; I think a lot of us just have a lot of self-doubt, a lot of copywriters have self-doubt about, “Should I go in this direction, or that, or…” So it’s a way of getting some validation on their ideas, of looking of things in a new way. And what they come away with, is usually a very definite plan: a marketing plan, a client-acquisition system, a way to frame their business, a focus… It’s not for pure beginners, but for people that have been doing it for a while and have the copywriting skills; it’s a way for them to kind of package themselves and their business in an intensive and immersive three-day setting.

Kira: I want to pivot before we rap, and ask you a big question, about, what do you think the future of copywriting looks like?

Steve: Oooh! That’s a good question, and it’s… You know, there’s people that think that—and I believe this to some extent, that—in a way, copywriting is in itself becoming commoditized, and by that I mean, there’s so many people doing it, that it’s easy for clients to get pretty good copy these days, and not have to pay a lot of money. So somehow, we as copywriters—so as far as where’s it going—we’ve got to get ahead of that game, and we got to stay ahead the curb there. because if all we do is just write copy, well guess what, you know? There’s A.I. that can write pretty good copy. There’s plug-n-play programs that can write pretty good copy. There’s good copywriters that are willing to work for almost nothing that can write good copy. So, we have got to somehow be a little more of an asset to our clients then just a copywriter.

We have to…. I talk about this all the time: we have to be idea-generators, we have to be giving our clients ideas that they maybe wouldn’t thought of without us. We have to be…we have to be problem solvers. So, those are two things I talk about a lot, is that we have be idea-generators and problem solvers more than just copywriters. But as far as where is it going, I think you know, for all this talk that A.I. is going to replace copywriters, and it’s all going to be done by machines and computers and robots and stuff in the future…you know what? Good, smart, intelligent, creative people are always going to be needed. It’s just, we may have to adapt the way we operate, and you know, how that fits into the whole landscape, but I believe that there’s always going to be a good opportunity for good copywriters, and good salespeople, and people who are good connectors, who are likable people. And if you can combine those three things, someone’s always going to want to hire you, and you’re always going to have work, and you can build your own business too.

But as far as the future of copywriting, I, you know…laughs…I don’t know. I mean, it’s kind of scary at some point because it seems like, what if…what if we could be replaced by robots? Laughs. I don’t know, but again, it’s the creative aspect that I just don’t think is going to be there, you know. Yes, you can have formula, and headline formula writers, and all this stuff, but the people who are generating ideas? I don’t think the big ad agencies in New York, I don’t think the Satchi & Satchi, and Ogilvy & Mather’s are going to all the sudden be done away with because…you know what I’m saying.

Rob: Yeah. Yeah, yeah. This has been a great interview, lots of interesting topics to cover and, you know, talk about, Steve. If people want to connect with you, where’s the best place for them to go?

Steve: Two places. So, my website, and then the other place is my Facebook group, Copywriter Cafe. Either way. Find me on Facebook, or find me on Or at Amazon: look for my book, The Freelancer Manifesto.

Rob: Great.

Kira: Awesome, thank you Steve.

Steve: Yeah! Hey, thank you for having me, this has been great. You guys asked a lot of really…laughs…I know you’ve been doing this for a long time, and are experts at this, but you asked me some really good thought-provoking questions, and it made me think. And I hope that some of these things have offered some value to your listeners.

Rob: Thank you so much.

You’ve been listening to The Copywriter Club Podcast with Kira Hug and Rob Marsh. Music for the show is a clip from Gravity by Whitest Boy Alive, available in iTunes. If you like what you’ve heard, you can help us spread the word by subscribing in iTunes, and by leaving a review. For show notes, a full transcript, and links to our free Facebook community, visit We’ll see you next episode.

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