Great Merch Starts With Better Questions And Better Process with Eliza Webster

Most people think a print shop makes money by “just printing shirts”. The truth is a lot more human and a lot more useful if you’re trying to grow a business without betting everything on one giant client. I’m joined by Eliza Webster, Sales Director at Cotton Street Apparel, a Winston-Salem, North Carolina screen printing and embroidery shop that helps everyone from local events to nationwide organisations build merch lines, uniforms, and promotional products that actually get worn. 

We talk about how Cotton Street evolved from band merch roots into a professional custom apparel company, and what they’d do differently starting from scratch: tighter SOPs, clearer team standards, and better early conversations with customers. Eliza shares how asking “Where are we going with this?” turns a once-a-year order into steady, predictable revenue, and why chasing a single “white whale” account can quietly put your cash flow at risk. 

Eliza also breaks down one of the biggest myths in custom T-shirt printing: markups aren’t about yachts and Bugattis, they’re about skill, equipment, quality control, and getting the details right when it matters. We get into outreach and sales habits like cold calling, planning with a printing-specific CRM (Sales Inc.), and building relationships across the industry instead of treating everyone like a competitor. You’ll also hear a simple mindset reset for overwhelmed leaders, plus what’s next for Cotton Street, including their community partnership with Camel City Goods and upcoming local events. 

If you got value from this, subscribe, share it with a business owner who needs steadier growth, and leave a review so more entrepreneurs can find the show. What part of the merch and sales process do you want to improve first?

Contact info:
eliza@cottonstreetapparel.com
https://www.cottonstreetapparel.com/
https://www.instagram.com/cottonstreetapparel/

Thanks for Listening. You may contact me or our team at https://billgilliland.biz/

All the best!
Bill

Please hit the subscribe button, leave us a 5 star review,  and share this podcast. You can reach me at williamgilliland@actioncoach.com or at https://billgilliland.biz/

Transcript

Welcome And Meet The Guest

SPEAKER_01 0:00

All right, everyone. Welcome to this week's episode of Epic Entrepreneurs. I am Cliff McCray with Action Coach Business Growth Partners, where we work with local business owners to drive real big ideas into real scalable growth. Today I'm excited to be joined by Eliza Webster with Cotton Street Apparel. Eliza, how are you doing today?

SPEAKER_00 0:17

I'm great, Cliff.

SPEAKER_01 0:18

How are you? Yeah, I'm doing wonderful and excited, really excited to have you on. So let's go ahead and jump right into things. So for those of you who may not know it yet, who are you, Eliza? Who is Eliza Webster and what is Cotton Street Apparel?

SPEAKER_00 0:30

Cotton Street Apparel is a print shop, screen

What Cotton Street Apparel Does

SPEAKER_00 0:34

printing and embroidery mostly in located in downtown Winston-Salem, North Carolina. We service our local community and several large uh entities with uh contract printing all over the U.S. Um, and we have a great time doing it. And we help start merch lines, uh, we help people outfit their uh crew who are working for them, uh, various other things too. So if you need a shirt, it's like I always say, help me help you not be naked. So if you need clothes, this is where you come to get your own custom clothing made.

SPEAKER_01 1:13

Yeah, we definitely wouldn't want that. So no, so you know, and who are you as a person, personally?

SPEAKER_00 1:19

Uh I am a unrepentant consumer of metal music, anime. Uh, I'm married. Um, I have a no kids, but I have a cat who is as much problem as a uh human child would be and praise that much attention. Uh so it's like uh I'm a mom, but I do a lot of uh side outside things. I staff anime conventions. I'm on the board of directors uh first saying Glass Playhouse, uh, which is a local community theater. So I do a lot of community theater outreach, and I spend a lot of time playing Magic the Gathering very badly with my husband and all of our friends.

SPEAKER_01 2:01

Nice, nice, nice. Now you threw out anime there. What's your favorite anime for anime?

SPEAKER_00 2:05

Oh, of all time, it's probably a very little-known anime from the 90s called Fashugi Yugi. Not a lot of people know it. It was very epic back in the day, and so old school anime people may know it, but if you started in the whole like Naruto Bleach era and into the newer stuff, you probably don't probably don't know it.

SPEAKER_01 2:27

Okay, okay. You say that Fashugi Yugi was that?

SPEAKER_00 2:29

Fashugi Yugi, yeah.

SPEAKER_01 2:31

Yeah, okay, yeah. No, I haven't heard that one. I'm gonna have to check that out. So appreciate the recommendation. Yeah, so go ahead and take us back to the very beginning. You know, what made you say, yep, I'm doing this, I'm starting that business?

SPEAKER_00 2:41

Well, uh, I I did not start this business. I have two great owners. Uh, our owners are Kyle Woodall, and he started the business in his bedroom in Florida. Uh many, many, many years ago, uh, he had a band uh and he couldn't find anybody to print shirts for them for a decent price. So he started printing and he got bought himself a little hand press and he got really good at it. So other bands started uh coming

How The Business Really Started

SPEAKER_00 3:10

and saying, Hey, uh, you want to help us out? So that all started in Florida, uh, and then he moved up here to North Carolina and he met uh Nikki Bowen, who is our other owner. Uh, and I knew Nikki uh because she and I worked together uh back at Hot Topic in the early 2000s. So Nikki and I were together over there. Nikki and Kyle stood, Kyle had started this business. Nikki came into it uh and left Hot Topic, and they became the driving force and the partnership that created uh originally what was called Machine Gun Graphics and has now uh changed names to Cotton Street Apparel back in 2021. Uh they I had helped out some in the past. They had brought me in uh at intervals when they needed more press hands uh and people to help with big orders. If Kyle was on tour, Nikki was printing stuff by herself, uh, and she's like, hey, come catch and fold t-shirts with me one night. And I was like, sure, girls' night at t-shirt printing, sure, why not? So 2021, uh, I get a call one morning and she's like, Don't don't go back to retail because we had all like left for the pandemic. And she's like, Don't go back to regular retail. She's like, come work here. And she's like, and I was like, okay, yeah, that that sounds good. I'll go work in production, uh, which is where I started. And then in November of 2024, uh Nikki came down and she looked at Kyle. She goes, I'm taking her, I'm stealing her, I need help upstairs uh in administrative, and I know she can do it. So I went from the production side of things to the sales side of things. And now I am the sales director for Cotton Street.

SPEAKER_01 4:58

Nice, nice, nice. Now, and you know, it seems like you know Kyle and Nikki pretty well, the actual owners. So if you if you you you know, and let's say this is hypothetical, you know, let's let's say if they had to start again from absolute scratch, you know, they had no brand, no clients, no safety net. What would you think they would do differently the second time around? Or would they do anything differently, you think?

SPEAKER_00 5:17

Oh, I think the second time around, because you always learn from uh past mistakes. I think the second time around, I think when you start something and you start something with the people you know and care about and your friends

Systems That Make Growth Repeatable

SPEAKER_00 5:34

and stuff, things at first can be kind of wild. Uh something we've learned as we bring new people on here, especially, is that we have very strong starting uh like start very strong guidelines and POS and and stuff that people have to follow and adhere to. So that it's uh all across the board. We're servicing our customers all the same way. Everybody has the the knowledge that they need to have to answer questions effectively, because I think when you start when you're just a group of people and friends coming from different types of backgrounds, because some of us have a very retail heavy background and some of us don't. When you're answering, when you ask one person one question, they may not have the same answer as the next. So I think that's one thing is starting strong and getting your entire crew on the same wavelength, but also to look at customers and really get to talk to them in a uh deeper area about, okay, this is great. You want to do this. Where where are we going with this? Is this a once-a-year type thing so that you can plan for that financially? Versus, okay, we've got this t-shirt, this part of your business, but I see you do all this other stuff. You have promo, you have bags and stuff. What do I have to do to make sure that I'm your one-stop shop for all of these items? And I think that's something that doesn't get discussed when somebody's like testing the waters with a new uh client. And that was something that wasn't always discussed, you know, early on, I think, into the business, especially when they were working mostly with like bands. Um, but now it's something that, you know, we really we really look at. And I think it's something that would have helped them grow faster back in the day had that been a discussion of, okay, cool, here's what you need to go forward. Here's where we can help you. Let's make this more than a one-time deal per year. Let's look at what we can do throughout the year so that it's a steady beat of income from the persons you so that you're not waiting for some sort of white, you know, the great Moby Dick, the white whale of a customer client. Because if you lose that customer client, you lose a huge amount uh of coming in. If you can get all your median clients and even some of your median to large clients to give you a steady stream of red revenue, you continuously grow uh and continuously stay on pace month to month with what you need to do.

SPEAKER_01 8:21

Okay, okay. So what would you say is one common m myth people believe about running a business that makes you laugh now when you hear it?

SPEAKER_00 8:29

Oh, that oh, yeah, that we that we make, especially off t-shirts, people think that the markups off t-shirts are for printing are ridiculous, that we're all millionaires and we have three boats and uh two two mansions and stuff like that. That's I feel like that's yeah, the my Bugatti, my Bugatti out back, uh yeah, all of that. They I I think that's a common misconception with a lot of jobs, but that everybody

Pricing Myths And Real Value

SPEAKER_00 8:58

is uh affected the same way. Our markups and and stuff are fair labor for, you know, it's very fair for what we do, the creative side of what we do. I think a lot of artists get that a lot. Well, I could do that. No, if if you could do that, you you'd be doing it. But you so when we're asking you to pay us what we're worth to do it, it's not you you're not paying just for the ink, just for the shirt. You know, it you're paying for the ability that we can put it on, we can run the machines, we know how to do and fix little tweaks, colors will be correct, everything will look exactly as you envision it. That's what that's what you're paying for going into a business like this.

SPEAKER_01 9:48

Yeah, yeah. So so be honest, are you naturally more of an entrepreneur or an employee at heart?

SPEAKER_00 9:54

A bit of both, because I spent my I I had my I had a I do I have little side businesses that I do. Um I bake wedding cakes, my mother and I have a craft business, small things like that. I think that's how I get my entrepreneurship type abilities really fired up, and then I bring that back into here. So even though I am technically an employee of my owners, I am have

Cold Calling And Sales Mindset

SPEAKER_00 10:23

got just as much drive to get out there and make this business grow and to see it flourish just as they do, because I want to see us all succeed. So I feel like that spirit's very alive and well with everything that I try to put forth day to day today, to go out there and get that new business, pick up that phone, talk to people. Lots of people are afraid of cold calling and stuff like that. You shouldn't. You shouldn't be.

SPEAKER_01 10:53

Yeah. Yeah, yeah. No, I mean that's kind of how I found you, honestly. I just kind of picked up the phone and gave you a call.

SPEAKER_00 10:58

Yes, you did. And I was like, I would be delighted, sir.

SPEAKER_01 11:03

Yeah, no, don't be afraid of cold calling out there, guys. It's you know, you never know what you're gonna get. I mean, yeah, you may get some people that, you know, maybe maybe be a little mean, but then you can have great people like Eliza here, so definitely pick up the phone and give that person that call. Don't don't hesitate. So, uh, you know, and I and I kind of like to ask this question here to kind of get a feel of how other people like to run things and how they kind of take care of things when they're away. So, how do you personally handle stepping away from the business? Are you a 7 p.m.? I'm not taking any more calls, I'm not doing anything else, or are you working around the clock? How do you handle that?

SPEAKER_00 11:35

I'm working around the clock. So I I cut off and I don't take, you know, any calls or anything past five unless it's, you know, them calling me. Like if it's Nikki or uh Kyle or somebody from the business calling me, I try to have a very good work-life balance. But there's always stuff at night strategizing

Work Boundaries And Staying Organised

SPEAKER_00 11:59

and thinking, oh, I've got to jump on this first thing tomorrow morning. Because I don't think I don't think I ever, I don't think any of us ever actually completely as much as we would like to 100% disconnect from a job when we're not sitting at it. But I like to when I'm away, I make sure at the end of the day I do my own little wrap-up and I go through and I have I'm very color-coded person, so I put all my checks and balances next to all the people that I talk to. If I know there's somebody I need to talk to first thing in the morning, I'll jot a note so that when I come back in and sit down, it's right here next to my computer. If I didn't take it home with me and say, okay, that's the first person I've got to contact, or that's the first thing that needs to get out. This is the first thing on my agenda today to get done before anything else. And then everything slots back in. But when I'm off the clock, there's still the brain is still computing, going, Oh yeah, I better make a note of that because I gotta do that tomorrow too. So I never really clock out.

SPEAKER_01 13:08

Yeah, yeah. And that's the biggest thing, right? You don't want anything to fall through the crack. So, you know, yeah. I mean, that's the biggest thing. You don't want to not reach out to that person. Could be a big, could be a big rule. You never know, right?

SPEAKER_00 13:19

Oh, yeah. And I I I if somebody like that's to say, if somebody gets me right at five when I'm getting when we're locking up and getting ready to go home, and I see it come through on my phone, I'm like, oh, that's fine. I'll sit in the car and I'll go back and forth with the person. I'll let them know, hey, you know, if it's something that can wait till the next day or something I need to think about, I'll be like, that's great. We are actually winding up for the day. Um, I've got this. Let me do a little research tonight, and I will get back with you tomorrow.

SPEAKER_01 13:50

Mm-hmm. So looking back, you know, what would you attribute most of the growth of the business to so far?

SPEAKER_00 13:58

I would say the the two things mostly for us would be the quality of our product and our ability to get out and do outreach with uh different people. We don't limit ourselves to like one type of client, which I feel like, you know, some businesses uh can't really help but do that. I think we're in a unique position where, you know, I'm doing that, you

Quality Outreach And Industry Community

SPEAKER_00 14:26

know, 5K charity run. Uh and for one person, I'm doing, you know, Peter Millar, Peri Ellis, you know, polos for uh a golf tournament is another thing I'm working on. And then, you know, we're printing uh metal shirts for a band. So we have this unique ability to reach out to all walks of life and to all different types of clientele. And we don't shy away from from any one uh section. And uh we're able to cover a lot of ground that way. And then the quality of our product, we've been in the game for a long, long time. And our production team, both our embroidery team and our screen printing team, are top notch with what they do. And then I devote personally a lot of time into research and making friends and colleagues out of a lot of um overseas production people. I've met and talked to a lot of reps and stuff. So I have a lot of friends for the promotional side of things that we do. So I can talk to people, get stuff in here fast with fast turnarounds so that we can print things for people. I've I've harbored a lot of great friendships that have really started to set us forward. Um, and I think just putting out a quality product every time and for us to get out and be willing to talk to people like you too. We've got a couple of things. Uh Nikki is part of the Women in Print Alliance, which has been a great, big helpful thing for us. That that's a major group within our industry, and just going out and reaching out to other people in your industry too, making friends with other printers, not seeing it all as straight, you know, competition day after day after day after day, and being able to, you know, reach out and get knowledge and give knowledge to to help other people because you know it's the whole giver's gain. You know, 99 times 99% of the time you give and then you'll get back. There are some people who'll stiff you from it, but the majority of people are good at heart. And if you give them a lot, they'll give it back to you.

SPEAKER_01 16:45

Nice, nice. So, and have you ever had to hire anybody before?

SPEAKER_00 16:51

I not well, I I semi-helped with our newest hire here uh since I knew I knew of her. We have opened a showroom in uh we we have a partnership with a local business called Camel City Goods, which is all Winston-Salem-based apparel that we've done the printing for for years. Now we house their um their brick and mortar shop in our front showroom. Uh, and we just brought on um a shop manager for up there

Hiring And The Camel City Partnership

SPEAKER_00 17:21

um who looks after the shop uh and is also our intake person for people who are coming to meet with us. Uh so I got to help hire her. Her name is Scarlett, she's a very nice girl. Um, I found out that she had uh left her former employer, and I was like, we were looking for somebody, and I was like, Nikki, I think this would be a good fit. I think uh she'll need to be trained more on fashion retail side of things, but she has good customer service skills, and that was uh enabling to bring her in. Um, but we've also talked about later on uh as we continue to grow, I will grow out, I will be my current sales director position. There will be another salesperson who comes up under me, and I will end up training them and everything that we do so that they're so that's that's coming. That's in the future. So I'm going to uh be working on that hopefully soon.

SPEAKER_01 18:23

Yeah, no, that's exciting. So all right, perfect. Yeah, so I appreciate that. So let's go ahead into what's called the quick fire round. So basically, what I'm going to do is I'm going to say one word, and then I want you to give me one word. The first thing that comes to your mind when you hear each word regardless to running the business, and then expand upon it a little bit as of why you chose that, you know, what you chose to what you said. Uh right. So first word is education.

SPEAKER_00 18:47

Education, you have to the first word that comes into my mind is it's a need. You have to be educated on the product that you sell, um, or else you're not going to be able to sell it to anyone. You need to know what goes into making it. You need

Principles For Planning And Execution

SPEAKER_00 19:01

to know how how and how to effectively make it and to market it to the people who want it. I'm sorry, I missed that. Planning. Planning. Planning. My CRM. I have a new CRM that I'm getting to learn and I'm working with. Uh it's called Sales Inc., it's wonderful. Uh, shout out to Kevin, who has put this together specifically for um us in the printing business. Um, and it has helped me become a better planner, planning my meetings, planning my steps to keep me in touch with all of my uh people. So yeah, planning I now equate right now to CRM.

SPEAKER_01 19:47

Nice, nice. Inspiration.

SPEAKER_00 19:51

Oh, inspiration. Art is the first thing that comes to my mind. Art, music, that's what inspired this entire business to start was music. So it's something that is very much a part of this, and because you know, printing's artistry, so yeah, that it would have to be art. Commitment drive because you have to have the drive and the commitment to keep the business growing. You have to be here and put in 110% every time you're here, even if there are days you want to be lazy, you gotta get in here, uh, you gotta contact everybody back, you gotta go out there and talk to the new people, you gotta find the new business, you can't you can't ever stop. Discipline structure. I have and have been a long part of my life with undiagnosed ADHD. So stuff like the CRM structures, notes, a part of that planning. It all has to uh go into that to keep me uh in line to do what I'm uh doing every day to keep me focused.

SPEAKER_01 21:08

Risk.

SPEAKER_00 21:11

Assessment. I feel like I do a lot of that. You have to take risks. Some you have to take risks on sometimes you take risks on clients, not knowing how stuff's gonna pan out most of the time, but whether or not they're bringing you something that's genuinely gonna be a good fit. I take a little more time, I think, than probably some of your average salespeople to really talk and get to know somebody to find out pretty early on um whether or not we are a good fit for what they're looking to do. And 99% of the time we are. Um, but the the parts of the time that we aren't, I have no problem helping them find somebody else who would be a better fit for them where they are currently. Because people remember that and they'll come back. To you when they're ready for ready for what you have to offer.

SPEAKER_01 22:04

And the last one is execution.

SPEAKER_00 22:08

Execution. A hundred and uh a hundred percent. Don't do anything half-assed. If you're gonna do it, commit to it. The product you put out has to be great. Um your customer service needs to be on par, even if the person that that you're doing it for is running you to death or giving you snark or whatever. You have to be like, that's just you don't know what's going on with other people, just breathe, walk through it, don't let it take your joy, do your job, and make sure that you, you know, you're giving them your hundred percent because they can never accuse you of not bringing your A game to the table.

SPEAKER_01 22:52

Yes. No, I love that. I love that. So, all right, yeah, appreciate you getting through that quick fire round there. So, yeah, a couple of questions here. So, you know, and and I want you to be as candid as you can on the next answer to this next question. But let's say if uh let's say a smaller business owner or maybe even a smaller time executive or so with listening to the podcast uh episode today with you, Eliza, and let's say they're feeling stuck or overwhelmed, let's say they're just not having a great week or even a great month, or let's say they're not even having a great start to 2026. I mean, we're already in the second quarter here, it's viewers already flying by. But what would you what piece of advice would you give to that person today to keep them from you know going over the edge, basically?

SPEAKER_00 23:33

I would say

Advice For Overwhelmed Leaders

SPEAKER_00 23:35

take 10, 15 minutes, 30 minutes of that morning, go do something that puts you in your happy place. Don't doom scroll or do anything like that. Pick up your favorite book, go to YouTube, find your favorite like YouTuber, find your favorite music video, listen to some music on Spotify, something that puts you in a mental state that will just bring you up. And then think about how you feel in that moment and apply that to the first thing you do that morning. So if the first thing you've got to do is enter something in your CRM, or the first thing you have to do is call a client you don't really like, or someone who's being difficult. Carry the joy that you had from that moment of solitude or that moment of enjoying something you really like and apply it to that person. Just hold that energy that you gave yourself, apply it to that person. When that's over, stop, breathe. If you have to refresh, do it again, do it again. Listen to that song again. Like I get songs stuck in my head all the time. Listen to that song again. Let it get you back to where you need to be, then do the next hard thing on your list. And then plan out at the end of the day, after you've done that, write down everything you get done. And, you know, so that you can look at it at the end of the day and be like, you know, today sucked, but I did all of this. I got all of this done. And if I did it all today, I can do it all tomorrow.

SPEAKER_01 25:16

Yeah. Okay, okay. So what's next for Cotton Street Apparel? You know, what should people be excited for in the near future?

SPEAKER_00 25:24

Oh, well, uh, the one thing we're super excited about right now. Um, like I said, we have partnered with Camel City Goods here in Winston. Um, we have there's new stuff coming. I've seen several, several new ideas, new shirts, new merch for that. And we're having a block party with a couple of our other local businesses. I believe it's Saturday, May 2nd. And we're closing

What Is Next And How To Connect

SPEAKER_00 25:53

down Brookstown Avenue here in Winston. Uh, and we are going to have a great party and a fun time. We're gonna do some live uh print uh with our original pull screen printer. Um so our original press will be outside, and we pressing by hand. Um, so that's gonna be super exciting. And then some of our people that we do um merch for are going to be here as well. So they'll people be able to see some of the other local uh Winston businesses we've been helping and uh getting all getting their all their cool merch and stuff out so people will get a chance to see that to sample their wares. Um and it's gonna be a good community fun time. So we're super excited for that, and we're super excited to grow and bring more people in. I'm super excited to have another salesperson here in the future, hopefully the near future, uh, so that we can expand and just keep uh going and reaching for the stars.

SPEAKER_01 26:57

I love it, I love it, I love it. So yeah, and what's the best way for some to connect with you or learn what you all do?

SPEAKER_00 27:03

Uh so we have a website, cottonstreetaparel.com. Uh you can pop over there. Uh, and if you look at the top, we've got uh a bunch of cool stuff. You can uh get in contact with us by uh needing. We've got buttons that need more information. Do you need a straight quote? Do you need some more information? Uh you can click that out, fill out our forms, it comes straight to me. Uh, and I'll be able to get with you and get you the information that you need. We've also got some fun um blogs and stuff on there as well. Uh, one of our favorites is it's not just a t-shirt where we talk about how t-shirts are more than you know, just something you wear. A lot of people keep t-shirts for years and years and years because it's a core memory. So that's a really fun blog, and I I encourage people to read it because it's a really good read um about the stuff that we keep um and how important screen printing can be to everybody.

SPEAKER_01 28:05

Any social media?

SPEAKER_00 28:07

Uh we are on Facebook. We are also on Instagram. We don't have a TikTok yet, but maybe we'll see. It's coming. Maybe we'll see. We're very we're we're more active on Instagram than anything else. But Instagram's a great way to see new stuff, both ours and Camel City Goods.

SPEAKER_01 28:26

Okay, yeah, yeah. TikTok is the way to go in 2026. Yeah, yeah.

SPEAKER_00 28:30

We're we're looking at it. It's uh it's gotta we gotta have a little more free time for social media to be able to do.

SPEAKER_01 28:39

No, definitely understand. Uh yeah, and Eliza, yeah, thank you again for coming on. This has been fantastic. Yeah, thank you so much for sharing your story, your perspective, and your real behind the scenes of building of the building the business. You know, it was great. Yeah, and anything, any last words or anything like that you would get want to give our audience here today.

SPEAKER_00 28:56

Just keep just keep doing what you're doing. Keep uh giving 110% and look for the things that you really love to do, and it'll make your job a whole lot easier if you're doing what you love.

SPEAKER_01 29:08

Yeah, no, agreed, agreed. All right, we appreciate everything you're doing for the community and wish you continued success. Thank you.

SPEAKER_00 29:14

Thank you, Cliff.