The 19 Marketing Podcast by Orange Label

Entrepreneur Edition with Terry Schilling – Part One

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November 18, 2021

Compelling copy doesn’t happen by accident. Orange Label writers Ashley Ruiz and Krystina Holford sit down with copywriter and copy coach Terry Schilling to discuss the details writers need to bring projects to life, how to keep copy consistent and the factors that make copy stand out in Part One of this podcast. 

Rochelle Reiter: [00:00:06] This is the 19. In 19 minutes or less, game changing insights from Orange Label, the leading response marketing agency for established brands that are driven by a fearless entrepreneurial mindset.

Rochelle Reiter: [00:00:24] Hello and welcome to The 19: Entrepreneur Edition, I’m Rochelle Reiter, President of Orange Label. Today, we’re going to switch things up a bit and do a roundtable talk on how to get the best from your copywriting team, whether that be your agency, freelancers or someone on staff here to share helpful tips and inspiration, we have Orange Label Senior Content Writer Ashley Ruiz and Copywriter Krystina Holford, along with our special guest copywriter and copy coach Terry Schilling. Since Ashley will be leading today’s discussion. I’ll let her take it from here!

Ashley Ruiz: [00:00:58] Thanks for joining us here on the 19 today, as Rochelle said, I’m Ashley and I’m the senior content writer at Orange Label. I’ve been with Orange Label for almost three years and what I love most about our agency and our clients is that I get to tell brand stories in a variety of different ways. In the past, I’ve really enjoyed interviewing small business owners for local and Latina Magazine. And now that I’m in marketing, I’m able to play a role in a wide range of brand voices, but enough about me. Terry, can you tell us a bit about yourself and your copywriting journey?

Terry Schilling: [00:01:29] Yeah, absolutely! So I am a copywriter in Chicago and I have only left really the Chicago land area to go to college. And there I was, studying to be a sports journalist, so I was really into the broadcast journalism and basically after that, after college did a little bit of freelancing from broadcasting side and sports reporting. And then I eventually worked for a startup, got into copywriting and marketing and got hired as a junior copywriter for an agency. And then from there just really got the entrepreneur bug, if you will, to do it on my own went all in on there and just wanted a little bit more variety from things I was working on at the agency and just felt that I could take it on. And, you know, here we are still like evolving my services, learning what I like, learning, you know, how to pitch those services efficiently. That also just pays the bills to at the end of the day, but really like fine things that I like to enjoy, you know, as well. But yeah, did not really think I’d get into copywriting from how I started. But the more I hear people who were like in journalism, the more I like, See, it’s such a simple pivot, you know, to go into marketing, and a lot of people have made a similar shift.

Ashley Ruiz: [00:02:36] Definitely. I had a bit of a similar shift with that as well. What would you say are the top three services that you offer?

Terry Schilling: [00:02:44] Yeah, I offer website copy, brand messaging and then working a lot with email marketing with different companies. So helping them almost as a consultant where we look at like their nurture series or help them build lead magnets and help them with newsletters. But that conversion copy side is really a main focus of what I offer to the brand messaging. But yeah, including that in email marketing, those are really the three big ones that I offer.

Ashley Ruiz: [00:03:10] Ok. Awesome. Yeah, I know we’re getting ready to have a lot of emails coming our way with all the holidays coming up as well.

Terry Schilling: [00:03:16] Oh my gosh, yes. All the cheesy subject lines. Yes, no doubt.

Ashley Ruiz: [00:03:22] Krystina, we know each other, but the audience doesn’t yet. Can you tell us a bit about yourself and why you love copywriting?

Krystina Holford: [00:03:28] Sure. I’ve been with Orange Label in a full time capacity for a couple of months. Before that, I was writing for Orange Label Freelance, which kind of is cool because it gave me a unique perspective of coming into different brands. Before that, I was doing freelance writing on and off for almost 10 years. I worked in in-house marketing and I majored in English, so I went in going, I totally want to be a writer. How do I be a writer? And got into the marketing side first and found people asking me, which I feel really lucky that that’s kind of how I got into it of people being like, Hey, can I pay you to write something? And being like, Yes, sure, and learn as I go. My first jobs came because I had a friend be like, I have to hire someone to write a press release, and I was like, What’s a press release? She was like, Google it and do it. And I was like, Great, OK. So that’s how I got my start, and I have kind of evolved from there and honed in on my skill set. And I love it. I love being able to tell different brand stories and yeah.

Terry Schilling: [00:04:36] That’s awesome! I like once you get that first invoice slash money to your bank account from like a writing job, it’s like, man, it’s just so validating that you can do it. Like, I got paid like forty five bucks to write, to go straight a children’s story, my first ever freelance project. And it’s just like now, it’s just obviously just transformed into so many things. But once you get that first one in a couple more, yeah, it’s super inspiring and motivating.

Krystina Holford: [00:05:01] That’s such a cool first project. How did you end up in that?

Terry Schilling: [00:05:05] I found that on Elance, like I was at the agency and wanted to do more work and earn some extra money, and so started looking at jobs and just apply to them like, Oh, this could be fun because I really didn’t know what I was looking for, you know of what to do and then just did that. And then it was interesting.

Krystina Holford: [00:05:22] That’s awesome. Sounds like a lot of fun.

Terry Schilling: [00:05:24] Yeah.

Ashley Ruiz: [00:05:24] All right. So when working on a new client project, what are some of the details you would say that you need up front? Do you prefer working with creative meetings or creative briefs, Terry?

Terry Schilling: [00:05:33] Yeah, great question. When I like to bring on a new project, someone reaches out to me, you know, learning a little bit more about what I do. And let’s say it’s a big website copy project. And if they have a creative brief where they there’s a link to their site, some deliverables that they’re looking for anything from like a brand style guide, brand messaging guide is always really helpful for me from the jump. And like I’ve learned, like to ask clients, too, of just like, where are they at, you know, especially if they’re a little bit more established in the branding side of things like do you know how you talk about yourself, like online through like social media, on your website, across the different channels? So getting an idea of that is super helpful. And if they haven’t, also then the light bulb goes off in my head that I can help them write that as well. So it’s kind of like an interesting situation there. But even just knowing that of where they’re coming from, it helps with the research side of things a little bit more specific questions to ask to help them establish that brand voice and tone. Our goal is to get their customer to act. So we want to have these different formulas and these different ways that we can get people curious to keep reading and ultimately click, you know, take advantage of it, offer what have you. But also just we want to know as much about the audience as possible. And if we know that, then we can establish the right voice where it just feels like we’re having a one on one conversation. You know, good copywriting feels like that conversation over a glass of wine, beer, coffee, what have you compared to reading a term paper, you know, to a 70 year old English professor.

Ashley Ruiz: [00:06:59] Yes, so true. You definitely don’t want to have to be reading it over and over again because no one is going to do that.

Terry Schilling: [00:07:05] Yeah.

Krystina Holford: [00:07:05] And it’s kind of, like you said, are they aware of their brand and their voice and everything? And I think that kind of starts the jumping off point for communication with clients. I know that that’s a really important for me kind of getting any information that I can like, Ashley said. Like a creative brief or like you said the email link, what do they have at our disposal that we can dove into? And even if we don’t use all the information like having it, just kind of hang out in the back of your head for me is super helpful to just have information and communication with them.

Terry Schilling: [00:07:40] Yeah, absolutely. And once I get an idea of the deliverables and where we’re going, and if I move forward with a project, I always like to have a questionnaire that they fill out that has more of those questions. So send those to like the key decision makers so I can get a good idea of how they talk about their business and how they talk about their audience as well. You know, also just liking to know who is going to be looking at this copy and reviewing it and like who we’re working on with all the team. That way, we can set those expectations of like, who’s going to be reviewing the copy and like how long it may take. Even those factors are, you know, important when learning, you know, more about the project and setting up a copywriter, you know, first success. Because if they have to wait and talk to an account manager, creative director, designer, all these things, it’s just like, let’s set up Slack. Let’s get a meeting to make it as smooth as possible.

Krystina Holford: [00:08:24] Absolutely.

Ashley Ruiz: [00:08:25] Yeah, definitely. I love that you send them questions like that. Sometimes I like to have those conversations with them, or I just get to hear what they’re saying about their brand and let them know this is something informal. I just want to hear how you conversationally talk about your brand, and I think sometimes they can get caught up on that. Well, like, Oh, this isn’t exactly the right words, but it just really helps paint that picture in my mind of the tone of voice they want to use.

Terry Schilling: [00:08:51] Yeah, absolutely. One of my favorite questions to ask is like if you had to explain what you do to a six year old, even like you get specific to like my seven year old nephew, it’s like, what would you say to them? Because if you can explain and like, get like a kid like interested or at least know what you’re talking about, then I guarantee you an adult will be able to figure that out as well. And so if you can simplify it like that, I think it’s a great starting point because sometimes the simple copy it works. You don’t have to make them feel or make you feel so smart with your copy. You can really simplify it. Don’t say dumb it down. It’s simple.

Ashley Ruiz: [00:09:25] Yeah, I love that. Where would you say that research fits into the copywriting journey?

Terry Schilling: [00:09:32] Oh, it’s huge, it’s like it’s like the oxygen for good copy, because without it, you know, I can’t breathe, I can’t speak to people. It’s just like, you need it. You need it to like live and I can have it exist. And so for me, it’s just like learning about the competitors reading online reviews. Great copy, it really comes from customer’s point of view. Like, we think that we know a lot of what we want to say because we’ve like the client has put all this time and they know what it does. But a lot of times they hire copywriter because they struggle with communicating that to their audience, you know, and their audience really like knows what they’re looking for. So if you can research and establish their pain points, what they want their desires, then you can speak to that much easier. You know, one of the toughest parts to hear is a copywriter. It’s just when a client will say it should only take you this long, any type of time frame. It should only take you like two hours, take you two weeks. It’s like, Well, I feel like you’re not including any of the research phase because, you know, talented copywriters, you know, at the end of the day, they know where to spend their energy and resources, you know, to really uncover good copy. And sometimes you can get a quote from a YouTube comment and Amazon book review, you know, and tweak that a little bit. And there’s your headline, you know? Yeah, research is huge.

Krystina Holford: [00:10:47] Yes, right. We’ve kind of touched on it, but getting into as much information as you can, like you said, like a good copywriter is going to be able to find that from different perspectives, different mediums…

Terry Schilling: [00:11:00] Yeah know where to look, yeah.

Krystina Holford: [00:11:00] Mediums, yeah. And then from there, like the timing might not even be as long as someone might think you can get going once you have everything like the actual writing might not take as long, but the back end work, the research is what takes even more time.

Terry Schilling: [00:11:20] Yeah, absolutely.

Ashley Ruiz: [00:11:23] If you’re working on something, even if you don’t use it for that certain project, then you can use it for them in the future. It reminds me I’ve heard with actors, sometimes they keep like a diary of what their character would say or something they go into that, you know, it just really helps that mindset that they know everything about it. In this case, it would be the brand like all dimensions.

Terry Schilling: [00:11:42] Yeah, a hundred percent. I recently had a client project where we were going through copy, and there’s a lot of stuff, you know, she liked. But like, we were going to include only obviously certain parts on the website, and she’s like, Can we make a document for like cutting room floor and just put all those things that like we really like that we could use for like a social media post, you know, on Instagram, LinkedIn or anything, maybe a future project. And like, I love that. And so like, I’m like starting to do that more with clients of just like, Hey, here’s a document of everything that we liked and you know that we can potentially use later.

Krystina Holford: [00:12:13] Yeah, that’s a great solution.

Ashley Ruiz: [00:12:16] Yeah, definitely. And I think that’s key is having it all in one place. I know sometimes I’ll write, you know, random notes and things. So if you have it in one place, it’s like because you you’re not going to remember, it won’t be an idea that lives in your brain.

Krystina Holford: [00:12:29] The Post-it Notes I have, it’s so terrible versus keeping it on a document.

Terry Schilling: [00:12:36] Yes.

Ashley Ruiz: [00:12:37] Right? We just need like a post-it pile because I know sometimes writing it, it does help you remember things, but if you just transfer it, so it’s all in one place in the end.

Terry Schilling: [00:12:46] Yeah, no, absolutely.

Ashley Ruiz: [00:12:54] Thank you for listening to part one of The 19: Entrepreneur Edition with Terry Schilling and Kristina Holford in part two of our podcast, we’re going to be talking more about the writing process and feedback.

Ashley Ruiz: [00:13:05] To learn more about Terry’s copywriting and copy coaching services, visit his website at If you have additional thoughts on this topic, send us an email. You can send questions, comments and more to

Ashley Ruiz: [00:13:20] Thank you to the people who made today’s episode possible. Orange Label President Rochelle Reiter, Senior Studio Manager Kelsey Phillips, Copywriter Krystina Holford and Senior Designer Micah Panzich, who edits the show. Be sure to subscribe to The 19 on iTunes, Google Play and Spotify, and, if you like what you heard today, leave us a review!

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