The 19 Marketing Podcast by Orange Label

Entrepreneur Edition with Terry Schilling – Part Two

More Episodes

December 02, 2021

In Part One of The 19 Entrepreneur Edition with Terry Schilling, Krystina Holford and Ashley Ruiz, we covered how to set writers up for success in the initial stages of a project. In today’s episode, we’re talking about the ideas that keep copy fresh and the tactics that make feedback constructive.

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.

Ashley Ruiz: [00:00:25] Welcome back to The 19: Entrepreneur Edition with Terry Schilling and Krystina Holford. I’m Ashley and I’m the Senior Content Writer at Orange Label. In part two of this episode, we’re going to discuss copy inspiration and feedback, so let’s jump back in.

Ashley Ruiz: [00:00:44] Is there any other ways that you find inspiration when you’re writing, Terry?

Terry Schilling: [00:00:49] Yeah, you know, it’s it’s so interesting, like pausing is so huge to me. Like, I feel like it took me a little bit longer than it should have for me to write like a draft that I feel good about, like sleep on it or even a couple of hours and come back to it, like, read it out loud and see like, Oh man, I thought this sounded good, but like, maybe I was staring at it for too long. I need to cut out like three words. So that’s always helpful and like inspiration for me. Like, like, I like stream and watch a lot of TV shows. Let’s do a lot of podcasts where they’re walking my dog working out or just, you know, free time, obviously. And so like, I have this passion, pop culture, sports, you know, the business side of things. So listening to podcasts and like like storytelling, I mean, obviously, it’s just so inspiring for me to like, write down ideas, whether it’s on paper, when it’s on notes. So like things like armchair expert, smart lists. You know how I built this code switch on NPR, just hearing like real people like, you know, the actors, but just like people like, you know, even just like activist journalists like tell stories, you know, just listening to how they do that and even like success stories like from how I built this super inspiring just to read out, you know, because a lot of times they like kind of like give the light bulb moment of like how we were able to create a product that people wanted. So you get a lot of customer feedback, and it’s that’s just helped me kind of think like how I can clearly communicate copy.

Krystina Holford: [00:02:09] It is interesting how much inspiration can come from Hollywood. We could say whether TV movie streaming, you mentioned some of my favorite podcasts other than this one. Yes, of course. And it’s interesting to like I have Hulu with ads. I don’t pay for the premium version. So it’s like watching something. You can get inspiration from the show itself, from the storytelling, and then you’re interrupted with a minute and 30 seconds of ads, and that can be inspiring in a different way and merging those two. I have found for myself has been a really cool source of inspiration, and although I do have post-its, I also have a notes file on my phone of just random things like Ashley and I were talking about, like even HomeGoods, like you walk in, it’s like live, laugh, love. Like, not that, but your brain can go, you know, take a little rabbit hole down like, OK, but what three words can we merge together?

Terry Schilling: [00:03:13] Yeah, absolutely. Like, you brought up such a good point with the like the Hulu ads, like, there’s some that like Catch my eye and I’m like, man, it’s such like products that I’ve never even heard of. Like, one was like primary clothing, which is just a kid’s clothing of just primary colors. So it’s just simple for parents to like, not have to worry about what’s on the design, just like if they want to wear purple, if they want to wear blue, we could get matching outfits. And just like hearing their headline of just how simple they talked about it, it’s just like they just spoke to the finish line at the end of the day, which can be. And that’s what makes them unique. That’s what’s different. And I’m like, that’s like a great example. And like, I’ll take that and I put it into like my newsletter and just kind of break it down. So people like just to give an example of like what this is of like not how to overcomplicate things.

Krystina Holford: [00:03:58] Absolutely. That’s so interesting. The end goal is ultimately what it’s you know what it’s there for, what it’s about.

Terry Schilling: [00:04:07] Yeah.

Ashley Ruiz: [00:04:07] Definitely. I actually recently signed up for your newsletter. When I signed up it has that welcome subject line. Instead of just saying welcome, it’s like I can finally say this to you and you know, you opened up and says thanks for joining. So I thought that was a really cool approach. And I’m like, Oh, you know, like, what is he going to say?

Terry Schilling: [00:04:25] Yeah, it’s so much fun messing around with those subject lines to see what works and like. For me, it’s just like I look at the line from like Joseph Sugarman, who wrote like the Ad Week copywriting handbook and I’ve like I mentioned this to people because it’s like, what is like copywriting to you? And I’m like, well, you can get people to like, read the read the first line and read the next and spend their hard earned money. Like, that’s your goal. And so then when you have that mindset or like when I have that mindset, I can like, find ways then to get them to do that. And me, it’s just like build like a genuine connection, you know, get them curious. So I can finally say this to you. It’s like I’m speaking to you, you know, instead of like at you. And then like, this is just really what gets you to open. Like, what is he going to say? And yeah, you know, like, I want people to feel like, you know, Terry sounds like a guy who was a sports journalist who got into marketing from there. He’s from Chicago. Like, basically, I just wanted to feel like it’s coming from me, like they’re making that connection. So yeah, it’s just, yeah, the newsletter is a lot of fun to break down, a lot of the copywriting examples and, you know, help people write better copy as well.

Ashley Ruiz: [00:05:36] Yes, definitely. Is there any certain ways that you like to come up with catchy subject lines in email?

Terry Schilling: [00:05:42] Like even for me, like having formulas in the back of my mind or just like that I go to to start writing a headline or subject line, like sometimes I’ll use that, but it just gets me to write something down and get started. You know, like how to formulas like the what is this formula like for the example of like, you know, I, you know, I can finally say this to you or just like, you know, don’t, you know, don’t start SEO strategy without reading this. It’s like, OK, what are they going to talk about in that email? But just like knowing the awareness level of your customers, like if you’re like an established brand and you are having this huge sale, you don’t really have to be that curious with them. Just tell them, you know, like this will sell out or like 50 percent off everything. Like, if I’m a loyal customer to that, I’m going to open that you don’t have to get too cute, you know, as well. So like knowing knowing your audience where they’re coming from is huge too.

Krystina Holford: [00:06:32] Yeah. Knowing when to get cute. I like that. Like, you know?

Ashley Ruiz: [00:06:37] Yeah, when does cute fit into this?

Krystina Holford: [00:06:39] Yeah, exactly.

Ashley Ruiz: [00:06:41] So talking about that end result, when you turn in projects to clients, how do you prefer to receive feedback Krystina?

Krystina Holford: [00:06:50] Feedback can come in any way for me. Again, going back to communicating what it is that we’re all trying to achieve because if we’re working with someone, we’re trying to arrive at the same goal, like whether it’s internal or external feedback. We’re trying to make the sale, get the user, get whatever the goal is. We’re trying to achieve that through great copy and I want it to be great for them and they want it to be great. So, you know, if there’s feedback, if it’s small, OK, if it’s larger, what did I miss? What can I go back? How can I look at this at a different angle or do something completely different and rework this piece, you know?

Ashley Ruiz: [00:07:34] Mm hmm. Definitely. I love that. That was actually one of the things Krystina first shared with our team when she started was, I don’t get offended easily, like, you’re not going to offend me. And I think that even sometimes setting the tone and those feedback meetings that you’re not going to offend me, this isn’t me personally or anything like that. This is writing about the brand. And like you said, you want the end result to be the best and you want people to read it and buy and take whatever action is the goal. Do you have anything to add to that theory?

Terry Schilling: [00:08:03] Absolutely. I think that’s such a huge skill, though, too as a copywriter is to put that ego aside, you know, and just make it a more collaborative effort. I always want to be easier to work with compared to just like promising something like the end result. Like this, I can almost guarantee that like, I will be easy to work with you and I want to make this collaborative and bring your vision to the screen and help convert. But honestly, like when it comes to feedback, for me, it’s like build up and don’t tear down. So it’s just like, be constructive with the criticism. It’s just like, how can we say this? Like, even if I’m editing something for like a writer that I’m working with, even it’s just like so subtle. We’re just like, this was really good. Like, let’s establish this like you did a really good job of like setting up an example here. Let’s add that in in a couple more spots here, and they’re like, let them know kind of what’s working to like, build up on that confidence. Don’t just say, Oh, this is great, because that just it’s really vague and we just don’t know what I did, right? Maybe what could be improved on? So, yeah, build up. Don’t just completely tear down. Don’t be so vague with the feedback.

Krystina Holford: [00:09:06] Yeah, I think being specific is super, super helpful. I know actually you and I have talked about this of, you know, if you want more, OK, what more do you want more literal words? Do you want more emotion, more education? What can I? What is it that you want more of? So that that can be delivered? What can I do for you?

Terry Schilling: [00:09:30] It’s just like, let’s like, let’s jazz this part up. It’s like, What does this mean? What are we doing here?

Ashley Ruiz: [00:09:35] Yeah, Like make it more punchy!

Krystina Holford: [00:09:38] Do you want your adverbs? Like what?

Terry Schilling: [00:09:42] Yeah, it needs to be more punchy. Yeah, it’s like, OK.

Krystina Holford: [00:09:46] Yeah. What does punchy mean to you?

Terry Schilling: [00:09:49] Yeah. Sometimes it’s like it’s hard to just even follow up with that with a question like, I just have to just like almost sometimes just assume what they mean there.

Krystina Holford: [00:09:59] Kind of takes like context clues.

Terry Schilling: [00:10:02] exactly. Yeah.

Ashley Ruiz: [00:10:05] I love the point that you made to Terry, where it’s like even good feedback can be expanded upon, and that’s something I think I’ve never really thought about before. It’s like, Oh, that’s good, and I just feel good about it. What resonated with you from it, And it’s really kind of making it that tactical point where it’s like, then this is makes it easier to replicate in the future.

Terry Schilling: [00:10:26] Yeah, absolutely. Like, I had a client. There’s a lot of stuff that you wanted like to add in and improve on, but you started like the feedback. Like, there’s a lot of strong things in here like this line was really good. I’d like to see more of that and then like going through the Google Doc and seeing and I’m like, OK, yeah, I see what she means there. But even that like. If you get an email or a comment right away, we’re just like, no, this doesn’t work because like the first thing you see, you’re like, All right, this may be a long day, but like even just like some type of confidence to keep going like of what you’re doing well and what we can incorporate, you know, because like, that’s so huge. Like as a copywriter, like especially my site, as a freelancer, it’s like I work alone. Like, I can’t really always bounce ideas off multiple people, you know? So like having that collaborative side with the client is, you know, it’s important for me, like if we can like, just go back and forth and talk about what’s good, what needs to be improved on?

Krystina Holford: [00:11:16] Definitely. Definitely.

Ashley Ruiz: [00:11:19] All right. So this is a big question as we wrap up. If you were to give one piece of advice on how brands can get the most from their writers. Wow, what would you say, Terry?

Terry Schilling: [00:11:28] Hmm. I’d say give them the goal and then let them find their path, let them be creative, let them do their thing and just trust them that they like one that they could figure it out, but that they’re going to do the research that they’re going to come up with some good ideas. You don’t have to micromanage them, you know, for so long. But yeah, just kind of talk about the end goal. And then just all right, now, let’s get there. And then just have them go from there. Because like writers, we like to we like to be creative. We like to feel like we’re creative. And if we feel like that’s a little bit there’s like a shield up there, we’re just like, Look, I feel like you already know what you want. Like, let’s just give you some multiple options here of what could work. Yeah, I think that’s that’s going to set everybody up for success because you, the client, can put their ego aside and be like, Look, this is this is good. We’re going to have fresh approach on this and we can talk this out and even combine ideas as well.

Ashley Ruiz: [00:12:22] Mm hmm. I love that. Krystina, any advice to share on how brands can best work with their writers? I know you have experience with freelance and agency as well, so it’s great to have that point of view.

Krystina Holford: [00:12:35] Yeah. Getting that end goal, that’s what it’s all about. We’re all on the same page. So first getting on the same page so that we can all try to meet that end goal. And I’ve said it so many times in such a short span here, but I’m going to say it again, communication, making sure that everybody knows what we’re trying to achieve. What’s the call to action? What are we trying to get out of this piece of copy? Whether it’s a tagline, an email newsletter or a blog post, whatever it is, trying to make sure that everyone knows what is supposed to happen so that the copywriter can make that happen again. Like you said, if you have like a copywriter that you trust to achieve that goal, you’re going to get it. Well, hopefully, but…

Terry Schilling: [00:13:25] That communication too, just helps with like the copywriter and the designer, because that’s a huge relationship and partnership there because like the copy could be really good. But if the design is bad and the copy doesn’t translate how you want it to, you’re going to have a tough time of converting customers and getting them to where they want to be. So like even that, just like knowing the goal for everybody involved, it’s like, All right, now, let’s put this call to action up here with the designer. How do we want? Where do we want want it to look like? It’s super important.

Krystina Holford: [00:13:54] That’s a great point. The relationship dynamic with everyone on the team and specifically with designers because great copy goes hand in hand with great visuals. So to make sure that those two things are working together and it’s really important.

Ashley Ruiz: [00:14:09] Yeah, that is a great point. Terry, do you ever work with the designers or have some communication with them during your writing process?

Terry Schilling: [00:14:17] Yeah, absolutely. I feel like majority of like, especially if I’m on working on a website project, you know, I love to include and just let them know like, I’m would love to meet with their designer on this and just like, talk through it, even have them involved with the project. Like, after this, I have to deliver the copy to see like what it looks like, because sometimes I feel like I may have a great headline and I’m like, well, this just is like three words too long. Like, We need to cut this down because it does look bad sometimes like to like. I make up mockups myself like in Canva, and we’ll like give that to client in case like they don’t have a designer yet, but at least we can see how it looks, because even then, from my perspective, I could see like, all right, this headlines too long. This subhead or feature is just, I’m saying what I want to say, but it clearly just looks like, you know, a big block of Lego and like on the page. So I need to update that. But yeah, I always recommend the copywriter and designer, you know, to partner up for sure.

Krystina Holford: [00:15:10] Yes, definitely.

Ashley Ruiz: [00:15:12] Exactly. Well, thank you both so much for being on The 19 today. I had a really great conversation with you both and learned so much and hopefully our audience does as well. Thank you, Terry, for joining us and Krystina.

Krystina Holford: [00:15:24] Thank you so much.

Terry Schilling: [00:15:24] Yeah, thank you both so much. This was a lot of fun.

Krystina Holford: [00:15:27] Yeah, thank you.

Ashley Ruiz: [00:15:34] Thank you for listening to part two of The 19: Entrepreneur Edition with Terry Schilling and Krystina Holford. 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: [00:16:03] 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!


Be a podcast guest

We love to host brand leaders and marketing experts to talk shop on our podcast. Send an email to with your area of expertise, hot take on a topic and any relevant information, and we will reach out if you’re a great fit!

Get our content

The best two emails you receive each month – our 19-minute or less podcast and our marketing blog. If you love ‘em, let us know. If you don’t, easily unsubscribe! (And let us know, we love feedback.)