How I Built A Multi-Million Dollar Cowboy Boots Brand

Howdy! I’m Will Roman, founder of Chisos Boot Company. We make damn comfortable cowboy boots and advocate for Texas land conservation.

I launched Chisos to the public in November of 2019. I did ~$20,000 in sales the first month and achieved ~$60,000/month within six months. Now we’re a multimillion-dollar small business—all with only four employees as of writing.

I spent a total of $9000 on advertising in the first two years of business. We are a local brand operating online. The following won’t apply to everyone, but these are the items I focused on to launch the business.

What's your backstory and how did you get into entrepreneurship?

I grew up with non-traditional parents. My dad sold things—whether cars or vending machines, he was always hustling. And my mom was a sign painter. I inherited a combination of entrepreneurial curiosity and artistic creativity, which I applied to my own t-shirt screen printing business, website and application design, and eventually to leather cowboy boots.

Systems are the key to growing beyond your limitations. One person can only push so hard; but a system can take the effort inputted and multiply its effectiveness.

Take us through your entrepreneurial journey. How did you go from day 1 to today?

Build a great product

Everything is predicated on having a product that speaks for itself. Our customers say there’s nothing else like a pair of Chisos boots. None of the below works if you aren’t delivering value to people.

I’ve worn cowboy boots my whole life. In my 20s, a back injury made wearing them painful. But since I’m a stubborn Texan, I would wear them anyways—and pay the price. One day I finally asked myself, “How hard could it be to make my boots?” And then I went down the rabbit hole hard.

I set out to make a more comfortable cowboy boot. I cut open my boot collection and discovered that the big boys were cutting corners and making low-quality boots 4, but marketing them as high-end. So I decided to fix that, too.

Skipping over a lot of hard work, the result is a badass boot that is in a class all its own. And, importantly, both the critics on YouTube and traditional media agree.

Build a real brand

Forget the word “authentic,” be real. That means not pulling punches and speaking like an actual human being.

Chisos doesn’t pretend to be some big company. There are now four of us here in Austin, Texas. For a long time, it was just me. And our small family-owned workshop in Mexico (where I was for months learning the process). I don’t hide those facts—I highlight them.

I’m also super pro-Texas and the brand reflects that. We give to Texas land conservation with every sale. For God’s sake, our motto is “Do Right, Love Texas.” The funny thing is, that even non-Texans respond well to it. People just like to see someone who stands for something and is willing to piss off a few folks along the way.

One example: we offer free shipping for Texans, but not for anyone else. This automatically applies based on a Texas address, but we also do free shipping for “expat” Texans as well if they ask.

Bring people along for the ride

Since the beginning, I’ve posted the journey of developing the boots on social media and on our email list. Everything from my sketches to things I learned along that week. It’s interesting for people; they get to learn about the process, give feedback, and become part of the story themselves.

Don’t hide warts, either. Every single time I post about how something went wrong and I addressed it, it gets a hugely enthusiastic response. And those posts where I feel that “People will see me as just a little guy, or an imposter, or just dumb” always end up generating lots of goodwill and encouragement.

I also joined cowboy boot groups on Facebook and (gasp) Reddit. The key is, that I became part of the community. Got on phone calls with other boot lovers to get their opinions. Shared my love for boots. Commented on posts from other people. I just did what I would do anyway if I didn’t have a business.

One time FedEx freight held up our shipment of boots. I decided that wouldn’t fly and so I rented a trailer, hitched it to my truck, and drove across the state to get the boots and drag them back to Austin myself. I posted about it live on our Facebook group and people were cheering us on along the way! It was so cool. People loved it.

Another thing I do is give out koozies and stickers and car decals like it’s going out of style. For 50 cents, if someone wants to put my brand on their truck, I’ll 100% do that all day long. Even people who don’t buy the product want to rep the brand. It helps spread the word and gets that person even more committed to a future purchase.

But at the very least, more and more people are seeing the brand.

Throw local events

Just host community events. Meetups. Live music. Whatever! Be the source of an awesome activity. This benefits the people who show up, but it also makes you look bigger than you are to all the people watching online.

Case in point: we threw a launch party. I struck some deals and reserved an entire bar (capacity of 400 people). Got some awesome bands—all local Austinites—to play. Even got a high-end whiskey, a beer company, and a water company to sponsor the launch. Oh, and had a buddy smoke some championship-quality brisket.

I submitted the event to every online or print calendar I could find in the city. This had three effects: 1) got people to show up, 2) made it look like we were everywhere, and 3) got us SEO and lots of content out on the internet about us.

Then I paid for local ads on social. FB can be expensive, I hear if you go national. But within a 40m radius, it is pretty cheap.

And the best part? I charged $20 for admission (donated to charity). We reached capacity and had a line down the street. AWESOME exposure and a ton of fun.

One other note on marketing: I printed out posters for the event (actually got one of the event's sponsors to pay for them). I stapled them all across town to those wooden covers they build on walking paths around construction sites. I would staple four in a row like they used to advertise old movies. So you can’t miss 'em. I even put them up directly across from the physical store of my biggest competitor. Besides being a ton of fun, they drove traffic (I asked everyone at the event how they heard about it).

Sprinkle in some awesome video content

I make video posts often and put some of them on our YouTube. They’re not the worst!

But every once in a while I invest in making some truly great content. Like the time I took a saw and cut my boots in half—along with two of my competitors. That video has tens of thousands of views on YouTube and thousands more on other social channels.

We get LOTS of comments that it was the deciding factor when someone was looking into buying our boots or not. So we stuck a link to it on the home page.

How are you doing today and what does the future look like?

Chisos is not being built to flip. This isn’t a VC play. We’re building the place our community can gather, both online and in the physical world.

Everything is long-term. Our boots are built to last a lifetime, but that’s just the beginning. We work hard to contribute to Texas land conservation to ensure that the wild places of Texas are still there for our grandkids. Chisos headquarters in Austin is a gathering place—monthly meetups, happy hours, concerts, birthdays, and yes, our showroom.

Our goal is to bring together those who value craft and community. It only gets better from here!

Through starting the business, have you learned anything particularly helpful or advantageous?

Systems are the key to growing beyond your limitations. One person can only push so hard, but a system can take the effort inputted and multiply its effectiveness. Our team is small—just four at the time of writing—yet we punch far above our weight because of the systems we’ve built together.

Don’t be afraid to do it differently. That’s the key to your differentiation and success. We are the only boot company to offer a boot made from wild hunted alligators, right here in Texas, that the founder hunted himself. And every order gives substantially to alligator habitat preservation. It’s something that can’t be done at scale, so our competitors can’t touch it. But we can do it. And our audience loves it.

Advice for other entrepreneurs who want to get started or are just starting out?

If I were to start a new product company today, I would make sure to consider:

• Supply chain chokepoints
• Cost of shipping and freight
• SKU count (sizes, etc, can everyone use the same version?)
• Lead times on production
• Consumable (do people consume your product, and then need to purchase more?)

Are you looking to hire for certain positions right now?

Not at the moment—but keep an eye on our cowboy boot blog for upcoming postings. And we’re always open to hearing from wholesome people.

Where can we go to learn more?

• Website
• Facebook
• Instagram
• Twitter
• Blog
• Email

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