Knowing Your Whys for Long-Term Brand Success | Anna Brakefield | Red Land Cotton

Anna Brakefield’s story begins on her family’s cotton farm in North Alabama, where she grew up surrounded by the rhythms of agriculture and the values of hard work, stewardship, and tradition.

Her father, Mark Yeager, instilled in her a deep appreciation for the land and the premium cotton it produced—lessons that would later inspire a business built on craftsmanship and sustainability.

After earning a degree in graphic design and marketing from Auburn University, Anna pursued a career in advertising in New York and Nashville. Though she thrived in the corporate world, her roots kept calling her back home, planting the seed for what would become Red Land Cotton.

In 2016, Anna and her father launched Red Land Cotton with a mission to bring American-made, farm-to-home textiles to market. Armed with her marketing expertise and a passion for storytelling, she shaped the company’s identity, ensuring that each product—crafted from the cotton grown on their farm—embodied quality, authenticity, and Southern heritage.

As Red Land Cotton continues to flourish, Anna balances entrepreneurship with family life, finding inspiration in the land that started it all. Her journey is a testament to the power of honoring one’s roots while embracing the possibilities of growth and innovation.

In This Conversation We Discuss:

• [00:00] Intro
• [00:39] Sponsor: Taboola
• [02:24] Building new ventures from existing resources
• [05:08] Turning constraints into strategic clarity
• [07:25] Sponsor: Next Insurance
• [08:38] Validating demand while building in public
• [10:21] Callouts
• [10:32] Blogging company journey for early engagement
• [12:03] Teasing progress to convert followers into buyers
• [13:48] Meeting customers where they are
• [17:15] Experimenting with traditional advertising
• [20:10] Sponsor: Electric Eye
• [21:19] Sponsor: Freight Fright
• [23:22] Investing in skills when hiring isn’t an option
• [25:18] Balancing creativity with marketing strategy
• [26:57] Matching products to the right channels
• [28:46] Leveraging cross-channel marketing effectively
• [30:09] Leading with purpose beyond just making money

Resources:

• Subscribe to Honest Ecommerce on Youtube
• Luxury American-Made Bedding & Towels redlandcotton.com/ 
• Follow Anna Brakefield linkedin.com/in/anna-brakefield-94389734 
• Reach your best audience at the lowest cost! discover.taboola.com/honest/ 
• Easy, affordable coverage that grows with your business nextinsurance.com/honest/ 
• Schedule an intro call with one of our experts electriceye.io/connect
• Turn your domestic business into an international business freightright.com/honest 

If you’re enjoying the show, we’d love it if you left Honest Ecommerce a review on Apple Podcasts. It makes a huge impact on the success of the podcast, and we love reading every one of your reviews!

Transcript

Anna Brakefield 

Intentionality that you bring to your brand is what will drive success. And everything else is supplementary to that. 

Chase Clymer

Yeah. The why. I think that's super important. I think some people, the why right now might just be money. I'll tell you what, when the money's not there, you won't want to do it. So you need a better why. 

Anna Brakefield 

Exactly. Yeah, it has to be bigger than money because money is going to come and go and you're going to feel depressed and want to give up on it.

Chase Clymer

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Hey, everybody. Welcome back to another episode of Honest Ecommerce. Today, I'm welcoming to show the co-founder and CEO of Red Land Cotton, a direct-to-consumer brand crafting bedding, towels and more all made here in the USA from cotton grown on their family farm in Alabama. Anna Brakefield, welcome to the show. 

Anna Brakefield

Thanks so much for having me. 

Chase Clymer

I'm excited to chat. I guess typically I'm asking folks, what are the types of products that you bring into the market there. But your intro greatly described what the products are. 

Anna Brakefield

Yeah. 

Chase Clymer 

But your story is so great. So guess, where does this story start? Does it start growing up on a farm? Does it start after college? Where do we want to begin? 

Anna Brakefield

Yeah. So I guess the story starts with my dad. So he's been farming cotton since the early 80s. He's one of six kids. And they grew up on a farm and out of six kids, he was the only one who wanted to make farming his occupation. And so we grew up quite literally in the middle of a cotton field. And I went to college and got a degree in graphic design and I moved to New York and I worked in advertising. And then when I got married, I moved to Nashville and this was in 2014.

And I just wasn't feeling it. It wasn't the quality of work that I was used to doing. And my dad approached me with this idea of creating a company that made bedding using the cotton we grew on our farm. And it sounded like a challenge. And it sounded like a way that I could use my background to come back and kind of work on the family farm in a different way. So that's kind of how I got to this place. 

Chase Clymer

Well, I've already got questions. So historically, the cotton that was produced on the family farm, was it just raw materials? Or did you have some of these things in place already? 

Anna Brakefield

No. Historically, it's just sold as a commodity. My dad put in his own cotton gin in 1994. So we grow the cotton, we harvest it and we gin it. I know that this is an e-commerce podcast. It’s not a manufacturing podcast. But, having the cotton gin allowed him to do his own cleaning. He stored his own cotton and he would, instead of selling it to a third party who would then sell it on the commodities market. He would do it himself. 

So I think in every way, he was trying to be as vertically integrated and owning the process so that he could get the best price for cotton that he could. So that was obviously a motivating and driving factor. Because the price of cotton is very set by global markets. It can be set by drought and horrible weather conditions and it leaves the farmer out of control. So I think trying to have control was a big motivating factor for him. But no, none of this was in place prior to 2015 when we had the idea. 

Chase Clymer 

Okay. So he has this idea and he wants to take this raw cotton that he has and he needs a partner, who better that he believes in his daughter to help come on this journey with him. What does that look like? What are you guys figuring out together? 

Anna Brakefield

Yeah. So we made a trip to Cotton Incorporated in Raleigh, North Carolina. And we took our classing grades of cotton and said, what can we make with this? And they confirmed for us that the cotton was [of] great quality. We could do whatever we wanted to do with it. The limitations really were within the supply chain here in the United States. We wanted it to be a product made in the USA because my dad grew up in the 80s and 90s. 

[He] watched the textile industry go away. And that was just central to who we wanted to be. We wanted to make it here. So really, the stipulation around what we can make here was more defining than what our cotton could make. So we determined that we wanted to make bed sheets because my dad's sister, [I] told you he was one of six. 

She did a post on his Instagram account and said that she would love a set of sheets out of that good looking North Alabama cotton. And we were also thinking, a set of sheets like that's pretty big that would consume a lot of cotton, better than a t-shirt or something. Those were the, you know, the really great thought out reasons why we landed on a bead sheet. 

So after we landed on what we were going to make, we started to put together our supply chain. We hired a retired textile guy in South Carolina. His name is Jack. He still works with us today. And he introduced us to all the players who are largely just still family owned businesses who have survived the large sucking sound and are still manufacturing cotton in the United States. And those are our partners today. 

Chase Clymer

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Chase Clymer 

That's amazing. How long did it take from meeting Jack to getting your first sample of that betting? 

Anna Brakefield 

So we started the process in February of 2016. I officially quit my job in May of 2016 and we had our first product in October. I recently did a post on our Instagram account. It's like [the] crazy things I did when I started this business. And I sold our first sets of sheets off of a charcoal drawing I did on a Squarespace site. 

That's, like I was wasting no time in trying to get a product to market. I was doing blogs, I was taking pictures, the whole way going to different plants and watching the process and taking my would-be customer along with me. So it was a pretty short startup time, really. 

Chase Clymer

Mm-hmm. And so you were immediately trying to sell this product. You weren't waiting until it was done manufacturing, which is something I'm highlighting here for all the entrepreneurs that are listening that are pre-having their product. Try to sell it right now. You're going to learn a lot more about it. 

Anna Brakefield 

Yeah. 

Chase Clymer

It might save you some headache if it isn't necessarily there yet or isn't solving the need that your customer wants. Trying to sell things before it's done is definitely a game changer in this industry, especially with how quick things can move. 

Anna Brakefield 

Absolutely. And you almost have product market fit before you have a product. If you can get people bought into the story that you're taking them on.

Chase Clymer 

Hey everybody, just a quick reminder. Please like this video and subscribe if you haven't. We're releasing interviews like this every week. So don't miss out. Now back to the interview. 

You were attempting to get customers before the final production. And so you mentioned that that looked like blogging that looked like bringing your potential customer along on this journey about, “This is how the manufacturing process works!” Was that just through your own website or what did [that] kind of that marketing look like? 

Anna Brakefield 

Yeah. I had a newsletter. So when you get on our site, you could sign up to be notified. And every time the first batch of cotton went through the supply chain. Every time it hit a new step, we were there. We went to the factory. We went on a tour and I blogged about it. And I told my customers about it. 

We took them out in the cotton field and talked about how the cotton is grown and why we feel like we're growing a superior crop here and all of the different regenerative practices we do. And this was all before we even had a product to sell. So I think when I got my first pallet of inventory, not from an overseas ship, it shipped from New Jersey.

But when I got my first pallet of inventory, I had 200 orders to fulfill. And that felt like the biggest undertaking in the world. My mom, my would-be sister-in-law came and we all packed those 200 orders in my dad's gen office. 

Chase Clymer 

I guess my question would be like, you're blogging about this whole journey and putting it out there. And some people feel like they're just like when they're blogging, they're putting stuff out into the void. How are you getting eyes on this content and then therefore converting those eyes into emails to sign up to the obviously, then some of them converted into those orders. 

Anna Brakefield 

Yeah. I think this was 2016. Organic posting on Instagram and Facebook could get you a little bit further than it does now. In some respects. But there were no viral reels or TikTok or anything at that point though. But we would post there and drive traffic to the site. Get the email signups. And then I would do text and email blasts saying, essentially, your product is at a new step in the journey before it gets to your door. That's how I teased it out. 

Chase Clymer 

Yeah. And I'm sure there was just in doing that and building that relationship with your customers, you probably made some advocates that were telling their friends. Like, “Look what I'm doing over here. Look what these people are doing. I think you might be interested in this.” 

Anna Brakefield 

Yeah. I mean, Southern Living did an article, our first season. And that was completely organic and happened just by chance. And I think that is due to the fact that we had created a little bit of hype. Nothing on a big scale. But this was all self-funded. Like I said, I split the baby and kept my job and built this on the side until I just couldn't do it anymore. And we just kept on going from there. 

Chase Clymer 

Yeah. Let's talk about what happened after. So you get the first production run, you have 200 orders already sold. How many were left in that production run? When was the next one? How did things start to compound? 

Anna Brakefield 

Yeah. To put anything through a manufacturing process, we had to write a pretty big initial order. So we made 20,000 yards of fabric in our first order. And there's about seven yards in a sheet set, roughly. So we had enough to have a very, I mean, I would consider this depressing now, but like a very solid Christmas season. I mean, launching in October, this is back when like pop-up markets and things were cool too. 

We did a holiday market in Franklin,Tennessee in early November. And it did so well. We had to meet someone halfway between Moulton and Franklin, Tennessee to get more inventory so we could continue to do the show the next day. So it was kind of a series of events that got us a little bit of momentum in those first two to three months. 

Chase Clymer

Yeah. 

Anna Brakefield 

And then reality really slapped us in the face in January and February as it does every year. But I think after the first 2 to 3 months, we felt like we had something. It was successful. People liked it. And we felt comfortable placing more orders in 2017. As I said, you get past the holiday buying season and then you get into January where you actually have to work for the orders. And that's when I felt like the real learning started. 

Chase Clymer

I want to get into that. I really do. But I do want to talk about something that you did at the beginning there that I think is what I hear a lot from other brands that have been successful is you weren't just waiting around for the orders to come into your website. You went to where your customer was, where you thought your customer was. 

You went to trade shows. You went to markets. You went to the farmer's market, right? Wherever you think that your customer might be. You went there. You met them. You attempted to sell them a product and you got their email, I'm assuming. 

Anna Brakefield 

Yeah. And because we sell pretty large products in multiple different sizes, it's not like I could take all the inventory to these different trade shows. So what I would do is have the samples there and then I would take the order and ship it to them. Especially if we went to one that was out of state. In the beginning, I mean, we went to Austin, Boston, and Atlanta. And gosh, we're in Columbus, Ohio. 

Chase Clymer

Hey, that's where I'm from. 

Anna Brakefield 

Oh, really? Yeah, I mean we were trying to get out there in any way possible that wasn't a huge massive expense. And I do think it's very much worth it. It's kind of a bummer that like most of the shows that we did aren't really a thing anymore. But I'm sure there's others that have replaced it. But it's good. It's good to actually get in front of people and meet them face-to-face and talk to them, especially as the founder of a brand. Be in the face. 

Chase Clymer 

Absolutely. Now let's talk about that learning curve once the holiday sales season sets in, you just place another... To you then, another large order of product. 

Anna Brakefield 

Yeah. 

Chase Clymer 

And I'm just gonna assume it's not moving as well as it did during the Q4 sales season. 

Anna Brakefield 

Yep. Getting a little scary, a little cash flow. “What are we going to do?" kind of situation. looking back on it, it's like, why didn't we lean harder into Google and Meta? But [I] got to learn, right? So what we did next was radio ads. 

Chase Clymer 

Interesting. 

Anna Brakefield

I know. On XM radio. 

Chase Clymer

How did that work out? I got to know.

Anna Brakefield

I mentioned that my business partner is, at the time he was 50 years old. He's a farmer. He spends most of his time in a pickup truck listening to XM radio. And he felt for sure that's what we should do. And it worked, but not as well as it needed to. So we spent a good bit of money on XM radio and saw growth. But it really took me. 

So I had my first baby in 2018. And I wasn't making enough money to put her in daycare. And I would stroll her around and listen to the Smart Marketer podcast with Molly Pittman and Ezra Firestone. And I took their course and I taught myself Facebook ads. And in 2019 is when we really like we were profitable and we were going and that is when the Facebook ads were firing. I felt like the queen of the world. The CPMs were great. Amazing.

And it carried on into 2020 and then 2021 happened and it just all kind of fell apart. But the learning experience was kind of strange for us because we leaned into an old school format of advertising and then came into digital. And now we're running kind of still a hybrid where we spend on TV almost as much as we do on digital.

Chase Clymer

I want to get into all that. 

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I want you to talk to me quickly about making the decision to learn how to do Facebook ad yourself.

Anna Brakefield 

Yeah. 

Chase Clymer

One, would you have considered yourself computer savvy back then? Was this something you would ever thought you could do? 

Anna Brakefield 

Yeah. I mean, I spent a lot of time on Google and YouTube. I taught myself how to put the website together. We did all of our fulfillment ourselves. So I set up what loosely we called our warehouse. So all of the technology that went into running Ship Station and everything else. So [I] felt like I was relatively prepared. 

But it was one of those situations where I was getting really frustrated and seeing that radio ad bill come in. And I didn't feel like I was getting the bang for my buck, essentially. 

Chase Clymer

Yeah. And just listening to podcasts and listening to what other people are doing. All these people talk about how awesome Facebook ads were. 

Anna Brakefield 

Yeah. And I'm like, “Well, I can do this.” And it was one of those situations where we didn't have money to hire anybody else to do it. So I'm going to do it. And I remember it was like $2,000 to take the Smart Marketer course. And I remember texting my dad and being, “I want to take this. I want to take this course to learn Facebook ads.” 

He was like, he still doesn't get it. He's like, I don't. He doesn't know. Even though he is on Facebook and posts and loves it, [he] probably spends too much time on it. But he was just like, “If you feel like it's the right thing to do, do it.” And it was. It was the right thing to do. And it's so funny because everything I learned during that, it's still applicable in different ways. But Facebook doesn't operate how I was taught to operate it essentially now. 

Chase Clymer 

Oh, yeah. It's definitely changed and that course is probably different, no longer exists or more or less money, who knows. But the point is that you took it upon yourself to learn that skill. Alright, how long were you noodling around in this course until you placed your first ad? 

Anna Brakefield

Oh, I placed it pretty immediately. That's kind of like my MO, I guess, is to do something and then ask for forgiveness later. Pretty much you can fix anything. You just have to start. And I was making my own creative because I have a design background. I was making my own videos. I was making my own artwork and launching as much creativity into Facebook. 

Then as I was going about the course, dialing in on the settings and creating the different target audiences and doing the different customer profiles. Honestly, like the real work of marketing and advertising that you kind of don't even have to do now and it's almost a little disappointing because I feel like you don't even have to really be good at it now to be successful. 

Chase Clymer 

Here's the... It's Facebook's algorithm. And the same with, so it's Meta now. But Meta and Google's algorithms are so insane. It's getting to the point where you can't be smarter than it. 

Anna Brakefield

Yeah. Yeah. 

Chase Clymer

It's just like, just let it do its thing and just feed it money and make sure your creatives are good. 

Anna Brakefield

Yeah, which is great. And it allows you to focus on other things, which is wonderful. But there's a side of me that's a little salty about it because I feel like I put in a lot of work and now other people don't have to put in the work. 

Chase Clymer 

Yeah. Do you remember how much you were spending when you first got started?

Anna Brakefield

Oh my gosh. $200 a day would have been a big... 

Chase Clymer 

That would have been like, “Oh, we're spending money now.” 

Anna Brakefield

Oh, yeah. But I mean, you could get a purchase for $10. It was great. 

Chase Clymer

And obviously with. Yeah. Especially back then, everything's, after 2020, everything just went up and never changed, which- 

Anna Brakefield

I know. 

Chase Clymer

It is what it is. Why I was asking a lot of around that is just I know there are some marketers out there, not necessarily marketers, founders, or people that work at smaller brands. That they have what I would call product-market fit. It sells organically on its own, but it's probably not moving the numbers that it could because they're just scared of paid ads. 

And I think these days, it's more expensive to start to see that traction on Facebook and Google. But I mean, if you see the traction organically, all Facebook and Google are going to do is pour gas on the fire and it's going to work for you. 

Anna Brakefield

Absolutely. And even with the traditional spend on a TV or a radio. If you are spending on those channels, it just amplifies that spend too. It's absolutely necessary. 

Chase Clymer

Oh, I think what's so unique and fun about your product is your audience is on those mediums. The USA-made textiles, those resonate with your audience. And those are high demos in those particular means. So I guess one thing, make sure that your product matches the place in which you're advertising. Because here's the, I use this example all the time. 

But if you're selling Harley Davidson inspired t-shirts, I don't think you're going to find much on Pinterest. It's got to make sense where you're putting these ads. But yeah, so...

Anna Brakefield

Yeah. 

Chase Clymer 

Back to you're not only still doing some radio, but now TV? 

Anna Brakefield

Yes. We don't do any radio now. I think if I was going to lean into that again, I would probably go about it the podcast route. But yeah, I mean, we spend, It's not 50-50, but maybe closer to 60-40. 40 % being an ad buy on Fox News. And it is super successful for us. And you can see it in the numbers. We started testing ads with them in the fall of ‘23. 

And you can see the revenue spike in growth from there. It's been a great, it's been a great partnership, but kind of to your point about like being scared to, to dip your toe into paid ads. I mean, that's just scary. It's scary to spend $20,000 on an ad.

Chase Clymer

Mm-hmm. 

Anna Brakefield

They made it really easy to test and to get proof of concept instead of having to make a big commitment. But as I said earlier, I think it has only amplified what we've been able to do on the digital side with that spin too. And our customer is there. Someone who cares about American-made goods is that audience. 

Chase Clymer

Absolutely. 

Anna Brakefield

So it makes sense. 

Chase Clymer 

Now, is there anything I didn't ask you about that you think would resonate with my audience? 

Anna Brakefield

I was having a call with a young girl yesterday who is wanting to do something similar with her family farm and have a direct-to-consumer brand. And the thing that I harped on to her because she has an Instagram, she has a website, she's not asking for anything. 

Chase Clymer

What do you mean?

Anna Brakefield

You know, she's not asking for an email. She's not plugging a product or telling the why. Like, why are you doing this? Why? And I think that that's what made our launch and continued success possible is the asking early and often for the sale, for the customer. And to be involved in this journey. You know, I said I graduated with a degree in graphic design in our senior project at Auburn. 

We had to concept a company and em do all the brand and marketing materials around it. And I essentially pulled that old project out and redid it for Red Land Cotton. And in that, you kind of set your intention for the why and the how. And who your competition is going to be and what the purpose is. And we're about to come up on 10 years of this business. And I went back and reread what I intended to do in 2016. And it is still the intention in 2025. 

And I think that intention is what drives success. There's a ton of tactical stuff and learning things that you can do along the way. But I think setting the intention for what you are going to do is really the true driver for success. We intended to create a product and create a revival in the American textile industry. And that is still what we preach and do today. 

So I think that the only other thing that I would add is that intentionality that you bring to your brand is what will drive success. And everything else is supplementary to that. 

Chase Clymer

Yeah. The why. I think that's super important. And I think some people, the why right now might just be money. But I'll tell you what, when the money's not there, you won't want to do it. So you need a better why. 

Anna Brakefield

Exactly. Yeah, it has to be bigger than money because money is going to come and go and you're going to feel depressed and want to give up on it. 

Chase Clymer

If I've been listening to this podcast, I'm like, wow, these sheets sound amazing. And you know what? I like my goods made here in America. Where should I go? What should I do? 

Anna Brakefield

Yeah, you should go to redlandcotton.com. And check us out. Our product comes in and out of stock fairly often, just given the nature of our supply chain. So we do a bunch of limited edition launches. And so if you like a style or a print that you see, we'd scoop it up because they don't last long.

Chase Clymer

Awesome. Anna, I cannot thank you enough for coming on the show and sharing all those insights with our audience. 

Anna Brakefield

I really appreciate it. It was fun.