Meet The Teachers That Grew a Side Hustle Into a 7 Figure Brand

Jeb Matulich and Brian Wysong are the complementary partners behind Tumbleweed Texstyles, a lifestyle business sharing the culture of Texas through clothing. In this episode of Shopify Masters, Brian Wysong of Tumbleweed Texstyles shares their bootstrapping strategy of growing a business from a side hustle along with their key retargeting tactics.

For the full transcript of this episode, click here.

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Show Notes

Store: Tumbleweed TexStyles
Social Profiles: Facebook, Twitter, Instagram
Recommendations: Klaviyo (Shopify app)

Reinvesting profits in order to scale your business

Felix Thea: Who was your partner and how did you guys link up?

Brian Wysiong: My background is advertising and I worked at a branding and marketing firm in Dallas and felt my heart lead me to wanting to help people. So I found myself teaching actually marketing in the career technology classes in Frisco. And I met a good friend, Jeb Matulich, who was the art teacher at the time. So we actually hit it off. We love the same lifestyle things, craft beer, traveling, and of course, all things Texas. And so I saw him sketching out something during a summer meeting. And I looked down at the sketch, I was like, man, that is awesome. That needs to be used for something. And so after going back and forth, we found ourselves starting a Texas T-shirt company where he would draw the designs and I would hustle and sell and do my best to try to get the product out there to customers.

Felix: How much of an investment did you have to make, and what did you do with that early investment?

Brian: We of course wanted to take a conservative approach being high school teachers. This is one of the things, I had a big dream of growing something big, but it really was just a side hustle. So, we each grabbed $350 each separately, pulled it together, $700 total investment to order our first batch of T-shirts that we printed from some college kids actually out of Denton. And from there, all was history. We sold those shirts, took back our initial investment. And then from there, took a couple of years, just kept on reinvesting the profits until we could finally one day pay ourselves without any stress.

Tumbleweed Texstyles’ complementary partnership has Jeb Matulich designing the t-shirts while Brian Wysong looks after operations. Tumbleweed Texstyles

Felix: So you've just been reinvesting back into the business and bootstrapping this entire thing the whole way?

Brian: That is correct. We are a lean company. We're pretty lucky and blessed. My wife had a photography business, and so, we utilized her skills in doing our photography and her graphic design. My business partner, Jeb, would do all the art and product development. And of course, I would do all the sales and account management. So we hustled making money from our real jobs, but bootstrapped and just kept on reinvesting the profits back into our business so that we could grow product options, more design options, and continue to grow it to where we felt very safe and comfortable to start paying ourselves and hiring employees or contract labor to help us continue growing.

Felix: How did you guys decide how to spend the money early on?

Brian: It was one of those things where we knew art, and I had a background in marketing. Neither of us really had a whole lot of history or experience in shirt printing. So we found some guys that we knew would be affordable, one. Two, came highly recommended. And so we went with them to print our first run of T-shirts, and we felt very comfortable with their artistic touch and quality, that it would be a great product. But of course, we were really conservative in our first garment. Making sure it's something we could afford. And when we started selling our product, we didn't spend a lot of money on advertising. We didn't initially start with a paid website. We used a system called Etsy to get kicked off to be able to make ends meet financially.

Felix: How do you stay focused and smart with the money now that there is more cash flow coming in?

Brian: For us, we didn't chase. We stayed true to who we are with our brand specifically. We wanted to make sure we lived out the lifestyle that we were promoting in our products. And so, for us, we didn't have to go spend tons of money getting photography in all parts of Texas. We were already traveling, seeing family and friends. My wife was the photographer, Jeb was the artist, I did the marketing. And so, right there in itself saved a lot of money. And as it relates to products, a lot of companies when they're kicking off, they think that “oh, we got to make everything perfect before we go.” But for us, instead of making everything perfect, we just ate the elephant one bite at a time, launched one shirt, and then two shirts, and then three shirts. And as income came rolling in and we saw the opportunity to reinvest that money, we expanded from T-shirts to sweatshirts, and then to tank tops, and then to glassware, home decor.

Felix: What were some things that you knew weren't perfect but were okay moving forward with anyway?

Brian: Well, our first garment. We didn't go with the most expensive blank garment. We went with something that was a little bit more affordable and we kept the hang tag in there, the label in there, so we didn't print our private label. And then as we grew, we slowly took out that tag and started private labeling it with our Tumbleweed TexStyles logo and name. And then from there, we were able to, as we had more income, grow into a better garment, which was more quality. And the good thing with that is in the long run, we had far fewer exchanges and returns because there were less issues with the products. And so instead of trying to hit a home run, we focused on trying to get to first base and then get the second base and kind of grow with the opportunities that arose with that based off the finances that we had.

Using experiential and relational marketing to grow your business

Felix: Where would you recommend other entrepreneurs in the apparel space allocate their time and money when they’re starting up?

Brian: I think first, people try to spend too much money on creating a perfect product, especially in the fashion apparel business. You try to hit a home run and you realize you used all of your resources and money and investment into the kind of putting your eggs in one basket. And so we started slow and decided to show progress along the way. Customers like seeing progress. They like seeing that the product is getting better, the designs are getting better, and not the other way around. And if you hit a home run on your first at-bat, anything after that, you're destined for failure because people have such high expectations.

Secondly, I would say marketing. For us, when we first sat down, instead of thinking, oh, Facebook ads and all these different kinds of advertisements, put money in a traditional approach in the local newspaper and create an ad there. We sat down and thought, let's focus on first relational marketing. I created a target And I said, who are our friends and family members that are the lowest hanging fruit? Let's go after them first because they're going to support us no matter what. Then the next outer layer was our neighbors or our coworkers as we're teachers in Frisco ISD. From there, we just kept on going to friends of friends. when we started, it was completely relational.

And then the second part of that was experiential marketing, where we have a story. We are two teachers, a marketing teacher and an art teacher that started our business. We provide a scholarship for anywhere from one to three graduating seniors a year. We have a story that resonates with people and that people want to support as well as hand-drawn designs that people want to wear. And so, we wanted to go to different festivals that people would be at that we can tell them our story, how they touched the product. And my business partner, Jeb, could tell the story of actually the design.

So, relational marketing, experiential marketing, and pop up shops. Those were our first ways of really growing our business without spending a lot of money.

Felix: Do you find that those products targeting a local consumer have scaled up as you reached a bigger market, or have you had to change your product catalog?

Brian: I think it's critical to expand because especially in the T-shirt business, everyone can make a T-shirt. Everyone can find a local printer. And so, if we continue printing the same design or continue printing the same theme of a shirt, people are going to copy it and it's going to be hard to sell a product and differentiate ourselves. So for us, Jeb and our design team is always thinking ahead of what's the upcoming holiday season. What shirt can we design for that holiday or what's the upcoming sports season or what's some trending elements in Texas culture.

That’s how we base our designs. Is by following the trends and following the demand of our customers. And how do we know what the customers want? It’s by utilizing social media. We have 40 some thousand followers on Instagram. So we're able to utilize Instagram and Facebook analytics as well as Google Analytics to really have a better understanding of the demographics and psychographics of who our customers are. Then we're able to better create products to reach our audience.

Felix: When you were first starting off, how did you get the feedback to improve and create better designs?

Brian: We pride ourselves, on handcrafted art. Therefore, people expect that from our team. Now, of course, we have some things that are font-based. But Jeb and Hillarystart everything in their sketchbook, and they draw it as a sketch. And then there's a process that goes from a sketch, processed into a digital form where they can add color. And then of course, it goes into the production side where we print the shirt. And that process of quality comes from little things such as adding more colors. When we started off to be thrifty, we tried to stick with one color prints only because it was more affordable. But as we grow, we start learning that people like additional colors on their shirts. And so, we are adding quality by adding more tones or more colors. But our team better understands the production process of how to utilize two colors to make three, four colors so that we're remaining thrifty while in the eyes of our customer, adding quality because there are more colors in the art. The other aspect is the growing product options. We take one design and we put it on a T-shirt, which is our core competency and it's successful. Then we quickly tried to promote that design to glassware from pint glasses, wine glasses, growlers, to home decor where people actually put it in their house, office, or dorm. And then, of course, hats, where we embroider it on to something that is not just graphic design, but now it's embroidered on to a hat or a shirt that people could wear, which takes it up, takes the value up to another level from a screen print to an embroidery piece.

Using social media to inform product development and generate leads

Felix: When it comes to T-shirt designs targeting a particular trend or holiday, how long can you expect them to last?

Brian: Tumbleweed TexStyles exist to not just be a T-shirt company but a lifestyle brand. And so, when we design our products, it's very much driven towards the lifestyle, the Texas culture, our products are very much seasonal based. The lifetime of our designs can be dependent on a holiday, could be dependent on the weather. And right now we currently have a few designs that are still our best sellers today that were our best sellers four or five years ago.

We have a shirt called the Texas Towns that Jeb created before the company ever existed. And that's still to this day one of our best selling shirts. And we right now have over 200 retailers throughout Texas. We have served over 1000 retailers since 2011. The differentiation of our shirts' success is not only dependent on what we do on Shopify on our website, but also on how our wholesalers are selling it and merchandising it within their stores.

Felix: In the design process, do designs typically originate from within the company first, or do you use data from Facebook and Instagram insights?

Brian: Designs are very much inspired by the lifestyle of Jeb, my wife, our team, and of course, myself. Those themes come from music, food - what I call the craft beer, wine, whiskey, - to wanderlust, the exploration of Texas. From the mountains to the rivers to the ocean. Most of our designs come from legitimately our lifestyle, our passions, our travels, the things that we do. But then there are many designs that come through the requests of our retailers. We have some large retailers that will have five, six plus stores throughout Texas and even the United States. And so, if they come to us asking for a specific theme, we have to determine if the volume is going to be worth our effort and time? And if so, then we make sure it represents our brand well and who we are and what we believe in. Then of course, our team will go to the drawing board and create something cool that will translate onto our website.

That's really the heart and soul and the inspiration behind our designs. But we certainly take in consideration of the analytics and information we gather on social media and on our website sales. As we see the demand grow in a specific theme, for example, plant-based shirts. We found that our yellow rose of Texas sold really well, and so we decided to create a Bluebonnet. And then Texas wildflowers. If we see a theme that's working, we definitely will exhaust that to make sure we're providing our customer the shirts that they want to wear to represent our brand and represent their pride for Texas.

A female model in a black t-shirt and male model wearing a white t-shirt, both with Tumbleweed Texstyles designs. — Nature, craft beers, food and lifestyle of Texas are the key inspirations for Tumbleweed Texstyles designs. *Tumbleweed Texstyles*

Felix: What specifically do you look at when you’re using analytics and broad data to create a design for a product?

Brian: Well, step one, my co-owner Jeb Matulich, he has an Instagram handle, Jebediahtexan. And that's kind of his personal Instagram handle as an artist where he many times will showcase sketchbook designs that he's worked on before we've even launched it. And based on that, we will evaluate likes and comments that are on that to determine if this is a design that we need to move forward into production on a T-shirt. So that's one way.

Secondly, we use Facebook pixels, where we're able to gather data of what gender is visiting our social media, and what's their behaviors. What images are they liking? What images that we're posting are they commenting on? Which ones are being shared? And then through that process, we're able to evaluate there are certain colors of garment that are more popular. And then we start evaluating. People have more city pride. And so, if we see those images being shared or liked, then we will do more city-based shirts versus Texas-based or lifestyle-based. We utilize that interaction to make judgments on what we should sell and make live on our site so that we're being good stewards of our resources and taking nearly as big of risk each time that we print a shirt and make it available to our customer.

Felix: So you are basically creating as much content as possible, putting it in front of your audience, and seeing what gets the most engagement.

Brian: We know who we are, and therefore, if we know who we are, we really know who our audience is because we're reaching people like us. And so, when we go to concerts, when we go out to eat with our families, when we are doing things in the community, when we travel in the summer, spring break, and whatever it might be, we see what the trends are. We see what people like. And it has nothing to do with our brand, but we start better understanding where the trend is going in Texas.

Felix: Can you describe the process of using experiential marketing, how you engage with the community, and the customers themselves?

Brian: As an entrepreneur or startup, you have to have the mindset of looking at everything that you do, whether it be sales, accounting, management, working with employees. Every aspect of the business is an investment for what might come. And so, many times, brands will go to events to sell their products solely focusing on the immediate sale. But for us, we had the desire to make sure we shook as many hands as we could, talk to as many people that we could, and tell our story. Tell them about how we got started and our mission and our purpose and where we hope to go in the future with our brand. Talk about the things that we love. And what we found is we started making a lot of friends. And when you make a lot of friends or tell your story and get a lot of buy into your brand, instead of spending money on advertising, you now have tons of walking billboards going out using social media telling people exactly why they should come to check out our brand. And so, at these events, we wanted to make sure we sold our product, showcased as many of our designs that we could, and create our booth space in a way that allowed people to come into the booth to shake our hand and hear a story.

Refining your story: creating a lifestyle brand that resonates with customers

Felix: How did you guys refine the story that you're telling about your brand?

Brian: As we tell our story, you kind of watch people's reactions to the words that we say or the things that we do. On social media, you see the things that people repost or they like. And through that process, you start finding the things that people appreciate and the things that maybe we appreciate more than what they do. Through that process, you start refining the story to tell the tidbits that people actually care about. And of course, what we're passionate about. We're not trying to sell something we don't care about, we're telling our story because we love it, we appreciate it and we're very excited about it. We're not telling our story just to sell a product.

Then, through conversation and interaction with people, you start realizing, okay, this five-sentence little pitch of who we are and what we do needs to be scaled down to one sentence. And then instead of using my words, to tell our story, let people see the printout, and we create a marketing card that we hand them. So they're able to read as a shop, and then we hook in at the end, “thank you all for coming. Check out our Instagram, check out our website.” Some kind of hook that connects them back to us.

That's my number one encouragement to starting entrepreneurs or people starting their first Shopify site. Shopify is a tool. It's an opportunity to be a hub. And so your goal is to do events. Utilize Facebook, utilize Twitter, and other social media. Utilize marketing cards. Utilizing email marketing to get people back to your site. You don't want to tell your story and lead people away. You want to tell your story, promote your product to get back to your site so that when they're on your site, you're collecting data. You're showcasing your product.

And then you're able to then reconnect to those people hopefully through a quality email marketing program like Klaviyo, where you're able to then continue reengaging those same people over and over as they hopefully buy your product and show interest in who you are and what you're providing.

Felix: Do you have any suggestions for creating a story that not only entrepreneurs but also customers relate to and identify with?

Brian: I think part of a story that resonates with customers is knowing who you are and what you do and why you do it. Seeing that there is a giveback component to the brand, that there's a greater good than just the product. But the reality is the story is great. But there's some math to it. A great story plus a great product plus a great creative design equals the excellence of who we are. That's exactly why we've been able to grow our product. A story alone is not enough. You've got to have a quality product. You’ve got to make sure people know that there is a quality product and, that there's a story behind how it was developed so that they have that desire to connect.

I think of English as a teacher; pathos, ethos, logos. Connecting to people logically, ethically, and emotionally. You’ve got to find a way that connects to people that resonates with them so they want to come back and purchase your products and support the cause of what you're supporting.

A male model in a black Tumbleweed Texstyles shirt. — Being able to share the brand’s story in a few short sentences proved to be crucial in fully understanding who they are as a team. *Tumbleweed Texstyles*

Felix: When moving beyond relational marketing and selling to complete strangers online, how are you able to generate those sales?

Brian: So there's a couple of components or channels of sales that we utilize. We have, of course, our B2C, through Shopify, which is our favorite part of our business. Secondly, our B2B. that's wholesale. Right now we have utilized a different website than Shopify to sell to wholesale. But with Shopify Plus - we've actually grown into the Shopify Plus program - we are bringing our B2B and our B2C under one house, one platform. But then we also have a custom where we do custom design work for different brands, companies, and corporations that we sell to. And then we're actually opening a brick and mortar store in Frisco where we're selling our products directly through our brick and mortar store so that people can come and see and touch and feel without paying shipping. And then from there, buy an extended amount of product on our site down the road.

Felix: Is this the progression of events you recommend? Going from B2C to wholesale, to custom design work and then a brick and mortar store.

Brian: Events are great because it's one weekend or one day and you go and sell your product, get it, go home. That's a less risky way to sell a product. But I think the natural progression is to have your own website so that you're able to tell people who you are and connect Instagram, Facebook, Twitter, Pinterest to your website. And then I think the third progression is wholesale. The thing is, once you get to wholesale, there's a lot more account management, a lot more touches as a realistic customer service.

I would say wholesale should come after typically the building of the brand and the selling of the product to the customer. And then having a brick and mortar store obviously is a bigger risk. It costs money to create your space. You have to keep it open, pay electricity on a regular basis. Hire employees. That's been our natural progression as the demand has grown to grow our business.

Felix: When did you know it was time to expand into different channels and how did you make that decision?

Brian: Initially, we never had the goal to do wholesale or sell on wholesale. It was just never even a thought in our minds. Our original goal was to do events and to sell on our website. But we actually started having retailers come to us asking if they could buy bundles of our product to sell in our store. So we started off more of a consignment model where there was no risk on the retailer, it was the risk on us. So we would basically loan them a certain amount of product, and they would sell it. And at the end of the month, they would owe us some money. And if it didn't sell, they could return the product.

And when we found that that was being successful and that we were able to increase the quantity of our printing, which allowed us to lower the cost of goods sold, we started realizing this is a great way to lower the cost of our product to be able to sell it on our site and make more money. So we were able to somewhat bring more focus to our website sales and enjoy our website sales more by providing more products because wholesale was driving the quantity to lower the cost of goods. It was just following demand and the inquiries of different retailers throughout Texas wanting to sell our product.

Using automated email marketing campaigns to re-engage leads

Felix: How do you use social media to generate email marketing leads?

Brian: Our website, Shopify, allows us to download various apps. And so, we have downloaded the apps of Klaviyo. And of course, through the functionality of Shopify, we've connected Facebook and Pinterest, Instagram, and anything that we can connect to it that we're utilizing on social media. It just naturally syncs together, and it's able to collect data and information.

As orders come in, that's one form of collecting data. As people sign up through our email marketing requests, like hey, join our TWT tribe, they sign up there to get coupons and different discounts. That all syncs into our Klaviyo program so that in Klaviyo, we're able to then send out email marketing. We're using social media to get people back to our website. And then we're using our website to integrate data into Klaviyo. Then in Klaviyo, we're able to automate processes where we have a welcome series. When someone signs up or buys a product for the first time, they automatically get a welcome email series. Email one tells people about who we are and what we do. Then in about three days, we send out a second email where it tells people about our product, how we create it, and the inspiration behind it. And then with the third email, we'll have the welcome series. We'll actually explain the lifestyle of our brand and give people an opportunity to buy a product with a coupon code or free shipping. We also utilize Klaviyo to do things like an abandoned cart - people add a product to their cart and they walk away. Well, they will receive an automated email to try to hook them back in with a discount code or a reminder to just try to get people to remember to buy the product that they showed interest in.

Felix: Speaking of automated email marketing, what is the entire life cycle of someone who joins your email list? Do you have any other automated marketing tactics?

Brian: We currently have more returning customers and new customers, which is great. But the email marketing that we send out, we don't send it out daily. We don't send it out weekly, always. We send out when there's a need or a new product or a reason to reach out to our customer. And what we found is that as we send more emails, the more our sales go up. And yes, from time to time, we'll lose customers in our email marketing because they might say they're no longer interested. But we also find that for every one we lose, we grow three. So we have customers that will forward it on to friends because there's a coupon code or a new product that we've launched. Email marketing, and of course, social media, are the two primary ways that we're able to engage our customers to keep them in the know as well as to provide quality content. And it's not about just selling a product. We might do the five things that Jeb and I are digging. And we might share a movie that we like or our favorite local restaurant. We might have a post that talks about some celebrity that was seen wearing our shirt. When we do our email marketing campaigns, it's not driven by sales, but it also is driven by quality content. Providing our customers with something of interest that they might find helpful throughout their weekly endeavors.

Felix: So what’s the balance between content emails and emails announcing a new product or pushing a sale?

Brian: We organize and schedule our launches based on our email marketing. So for us, we find sending our emails out on Friday is the optimal time for us because people are expecting those emails. And then they have a whole weekend to read the email and potentially make a purchase. We find that consistency is very important to email marketing campaigns. But then also, utilizing holidays and special events to package the launch of products or to package the promotion or sale so that it's not just something random but there is a tie into either Christmas, Black Friday, Cyber Monday. Texas Independence Day or national taco day. So we try to find ways to tie it in that makes it fun or more engaging for our customers.

Felix: You mentioned abandoned cart, what seems to work best for re-engaging a customer who has abandoned cart?

Brian: The most success we found from our abandoned cart campaigns is that it is sent within 24 hours. And not only that, but there's some sort of coupon code attached to it. Now, we found that sometimes people might purposely put something in the abandoned cart to get that discount code. But we're okay with that if they make the purchase. So, I would say the most important thing is within 24 hours, and then have some kind of hook that reminds them to come back. And then in our campaign of abandoned carts, it shows the abandoned cart or the products that were in their abandoned cart. And it's a quick reminder of oh, yeah, that's the product that I like or I love. Because sometimes people might add something to their abandoned cart or their shopping cart when they're on the fly like at a red light or when they're at work. It's just a quick reminder to say, “Hey, don't forget this, you need to buy it while supplies last.”

A female model wearing a grey t-shirt by Tumbleweed Texstyles. — Abandoned cart emails along with a coupon code is a winning combo for Tumbleweed Texstyles team to turn those who are browsing into customers. *Tumbleweed Texstyles.*

Felix: When scaling beyond a T-shirt focused business, how did you decide what the next move was? What new product strategy did you use?

Brian: With our product, we found that people appreciated the design more than just the garment. We knew it was a natural fit to put our art on decor because people were asking for that. We wanted to provide an opportunity so that people could take our art and put it in their dorms or their office to showcase their pride or their lifestyle. We also found that a lot of our customers, including ourselves, love to just casually sit by the fire and drink coffee, or sit outside and drink our favorite drink. And so, that is where our progression to glassware came - because we found that it was easy to put our design on that same glassware. But it's a way to expand that design to a new product that still represented the same lifestyle. Now, we're actually in the process of growing into a custom button-up shirts that are also representing the lifestyle of hiking and fishing and kind of a preppy lifestyle. It's not just a T-shirt, but it's taking some of our designs and manufactured into a fresh new buttoned-up garment. We found that you don't always want to wear a T-shirt if you go on a date or if you want to go out somewhere nice, you might have to dress a little bit nicer. So, we've progressed to take those designs and put them on something that people can wear for a little bit more of a nicer or preppier occasion.

Felix: If you could focus on only one thing, what is the most important thing for you to focus your time on?

Brian: I love focusing my time on managing people or interacting with people. So I love management, encouragement, inspiration, motivating. And I'm a visionary. I like setting vision and creating goals and standards. And then having a team that can get in the nitty-gritty micro parts of our business that can make it happen. And I also love marketing and branding. I love communicating the essence of who we are and everything that we do. Building consistency in our look, in our colors, in our fonts, in our branding, so that people can see a connection in all the different elements of our marketing and our product so that they keep on coming back for more. I would say management, marketing, and branding are the three things that I love most.

Felix: What is the goal for the next year of the business?

Brian: We're opening a new store in Frisco, a brick and mortar location that I'll be sitting in every day working on my computer and then helping serve our customers as they come in. So, a goal is to expand our employees, to have people that can help work in the store, to grow our design team because right now, we're unable to keep up with all the design work that we have and that we can take opportunities to pursue. And to create more efficiency. Utilizing technology to automate our emails, to automate customer service, to automate the things that technology and Shopify provide us the opportunity to use so that we can utilize people to make those things happen and to solve problems.

by Felix Thea

Last updated Aug 15, 2020