How The Hat He Once Used to Hide Behind Became The Cornerstone of His Calling: Derek Welborn of Saints Western

There is a version of the Saints Western story that sounds almost too good to be true.

A pastor learns how to make a hat at home, uses nearly all of his vacation time to try selling them at Round Top, and meets a veteran vendor who sees something in him and buys thousands of dollars of equipment to help him keep going.

Then Brandon Lake calls.

Eventually Derek Welborn finds himself on tour, then inside a Nashville house making custom hats while Lainey Wilson, Thomas Rhett, HARDY, Nick Jonas and some of the biggest songwriters in music move in and out of the rooms around him.

It is a great success story.

It is also not where the story begins.

It begins with a man in his mid-30s watching his hair fall out in clumps, and a hat he did not wear to stand out.

He wore it to hide.

In 2020, Derek developed alopecia areata, an autoimmune condition that causes hair loss. There was no gradual adjustment.

“One day I had hair, the next day it’s out.”

First came one bald spot. Then another. Eventually, Derek says, it felt as though the hair loss was taking over his head. 

It was coming out in clumps.

“It was a really hard thing to navigate with my identity.”

So he covered it. Baseball caps first, then a Stetson. For nearly a year, Derek says he would not leave the house without a hat on.

“Okay, God, if You choose to heal me, I’ll praise You. And even if You don’t, I know it’s part of my story and I’ll figure it out.”

Long before Derek became a hatmaker, he was already an unusual combination of athlete and artist. Baseball was the plan. He played through high school and into college, eventually attending Lee University.

But he was also the kid who laid his outfits out on the floor the night before school.

“I was always into style, always into fashion.”

He painted, noticed what people wore on television, searched for versions he could recreate and then changed them enough to make them his own.

His career eventually moved in a different direction: ministry.

Derek first began serving young people in a juvenile detention center. After college came a series of church roles, first as a youth pastor in Georgia and later in Austin, where he eventually became a campus pastor at a downtown church.

He describes ministry as deeply meaningful, but also heavy.

“You’re bearing the weight of other people’s burdens and trying to navigate while trying to manage your own stuff and your own family and your own things.”

At one point, while spending his days counseling and helping other people, Derek realized he needed help himself, so he went to counseling.

There was another part of ministry he loved deeply, too: people.

After a year of wearing hats because of his hair loss, Derek started looking at custom hats online. He loved them, but he did not love the price.

“So I was buying cheap hats and trying to make them look cool.”

Eventually curiosity won.

“I wonder if I can learn how to make these.”

Since he had been following so many hatmakers online, social media began serving him ads for raw materials. Around Father’s Day, Derek asked his wife, Jill, if he could order enough supplies to try making one himself.

He bought a hat block on eBay, but it was not even the right kind. It was a fedora hat block. 

So he taped a hat stretcher to the bottom of it to get the crown depth he needed, used a clothes steamer and figured the rest out as he went.

Somehow, the first hat was wearable.

“I was honestly shocked because I didn’t really know what I was doing.”

Birthday gifts became felt, and he made another hat, then another. Conveniently, he and Jill had the same head size, so she started wearing them too.

People noticed. They would compliment Jill on her hat.

“Oh, he made it,” she would tell them.

And eventually came the obvious question: You make hats?

Derek would joke,

“Well, I make me hats.”

He only had one size block, and the wrong type of hat block at that.

A man at Derek’s church learned he was making hats and discovered he could only make one size. He offered to buy him a complete set of hat blocks.

Derek resisted. The man insisted.

“Paul was a tentmaker. You’re a hatmaker. I want to bless you. Don’t take this from me.” Derek finally said yes to the unexpected blessing. 

Then came Clint Hough. A mutual friend, songwriter Jesse Reeves, thought the introduction made sense, since Clint was a longtime Round Top vendor at the Arbors with decades of experience importing goods from Mexico and knowledge of the hat business. Maybe he could help Derek find better materials?

Derek and Clint went to lunch. Four hours later, they were still talking. Eventually Clint started telling Derek about Round Top.

“Why don’t you come and sell your hats in my booth?”

There was one fairly significant logistical issue: Derek was still a full-time pastor. So he asked for two weeks off, using essentially all of his PTO to see what might happen.

His previous experience with Round Top had been brief. He and Jill had visited once with two small children on a cold day, and the kids did not want to wear their jackets. It was a short trip to say the least.

He had heard of Round Top too, of course. He just had no idea what he was walking into.

Derek set up in the corner of Clint’s booth and started selling. He sold around 12 hats.

Not enough to quit his job, but enough to realize, there was a place for Saints in Round Top. 

After the show, Clint told Derek, “If you want to do this, I would love to help you and your wife.”

There was no contract or repayment structure. Clint simply asked him what he needed. Derek gave him a list of equipment and supplies for making hats, and Clint bought roughly $15,000 worth.

“It wasn’t like, pay me back when you get it. It was like, I want to bless you and want to help you.”

Round Top has always been built as much on relationships as things. Derek’s story is one more example of that.

Clint’s investment in Derek did not stop with equipment. He took him to León, Mexico, where they went looking for a boot manufacturer and found a factory that had been operating for around a century.

They began sketching boots, tested a small run at the next show and sold enough to keep going.

For roughly six Round Top shows, Clint worked alongside Derek, helping carry inventory costs, introducing him to the rhythms of the show and teaching him a business Derek was still learning in real time.

Eventually Clint told him he was finished. It was Derek’s now.

The message, as Derek remembers it, was essentially: I taught you Round Top. You’ve got it.

Round Top gave Derek a place where the two sides of his life overlapped in a significant way.

“What I love about that retail space is that it allows me the freedom to create, and then the pastoral side of me with people and just meeting people, hearing their stories. It kind of merged the two.”

Years earlier, Derek had loved that his downtown Austin church met inside a bar because it provided common ground for people who might never feel comfortable walking into a traditional church.

There is a similar instinct behind the way he approaches Saints: create something, welcome people in, and hear their stories.

When Derek first started making hats, there was one person he dreamed of making one for: Brandon Lake.

Lake had become one of the biggest artists in Christian music and, importantly to a new hat maker with a dream, he wore hats.

“Man, it would be cool to make him a hat one day.”

Through mutual friends and Nashville connections, one of Derek’s hats eventually made its way into Brandon’s world.

Then one Saturday morning, Derek’s friend David Leonard FaceTimed him around 8 a.m.

“Dude, sit down.”

David had been hanging out with Brandon the night before.

Brandon wanted a hat.

Derek could hardly believe it.

“Bro, that was my goal.”

David’s response would stick.

“Well, you better dream bigger because God did that, you know, in a few months.”

Derek made the hat, and he and Brandon stayed in touch. They discovered they shared a love of fashion, style, creativity and dreaming up what might come next.

Their friendship developed for roughly a year and a half before they even met in person. Eventually they did, when Brandon came through Austin for a show.

Afterward, Brandon looked around at the collection of creative people gathered there and said something Derek remembers clearly.

“I don’t know what God’s doing, but He’s doing something with this crew right here.”

Later, during a Round Top show, Brandon called. He had always wanted to build a brand but did not have the bandwidth to do it alone.

“What if I came on as a partner, and we do this together.”

The phone call opened another series of doors.

Derek brought in Austin entrepreneur Wade Lombard for business guidance and Ryan Case, who had years of fashion-industry experience. With partners and investment behind the company, Derek finally had the opportunity to step away from full-time ministry and give Saints Western a real shot.

While Derek was still pastoring, he had another idea: mobile retail. Maybe he could renovate an Airstream, hire someone to travel with it and take Saints to events without leaving ministry. 

He started looking. At Round Top, he asked around the Arbors to see if anyone knew of one for sale. Then one day, while walking through the show, a woman called out to him.

 “Hey, preacher, I got an Airstream.” 

Derek went to look, and eventually bought it. Later, as Saints’ partnership with Brandon was taking shape, Brandon had an idea of his own. The Airstream was being renovated, and he had a tour coming. “Bro, you got this Airstream. Let’s take it on tour."

Suddenly Derek had about three months to finish the renovation, build inventory and prepare Saints Western to travel alongside the tour. From the outside, going on tour with Brandon Lake sounds glamorous. Derek’s version involved selling before and after the shows, packing everything up around one in the morning, driving four or five hours to the next city and sleeping at rest stops. He and Ryan eventually completed around 25 tour dates. During one especially brutal stretch, Derek estimates they slept eight hours over four days. The reality of building a business and a dream requires a whole lot of grit. The high of seeing dreams realized and the grit to keep going. 
“It was not probably the safest thing in the sense of like, we were exhausted," Derek recalls of the tour days, but also reminices how there is nothing like it.

Eventually they brought in additional help. City by city, more people were discovering Saints Western. Then came Nashville.

In December, Brandon called again. He was putting together a songwriting retreat and wanted Derek to come make hats.

What started as a relatively small gathering grew. Derek brought his equipment and set up in the center of the house, while songwriters worked in rooms to his left, upstairs and downstairs.

Every day new artists came through: Lainey Wilson, Thomas Rhett, Russell Dickerson, HARDY, Nick Jonas and many more of Nashville’s artists and songwriters.

Derek would start making hats around 9 a.m. and sometimes work until one or two in the morning. In one week, he made around 21 hats.

The writers made 47 songs.

He could hear the music being created around him while he worked.

“What am I doing here? This is crazy.”

Ask Derek what he wants someone to feel when they put on a Saints hat and the story circles back.

“I wore hats because I was trying to hide.”

Today, his goal is almost the opposite.

“What story do you want to tell?”

Derek makes stock hats, ready-to-wear pieces and fully custom hats, but the transaction is not the part he seems most interested in.

What matters more is the person sitting across from him.

“I want to help tell their story.”

And ultimately:

“I hope that they feel like number one valued as a person. And then number two that their story’s being told.”

Walk into Saints Western during Round Top and Derek wants you to feel all of it.

“I want people when they come into our booth. I want them to feel all five senses, like from the smell to what they touch and all the things because it creates memories.”

The furniture, the clothes, boots, hats, vintage pieces and art are all layered together.

“I try to make it feel like home for people.”

What shoppers do not necessarily see is what came before the finished booth: Derek moving couches himself, setup and teardown, long days, his kids brushing hats, Jill stepping in wherever she is needed and peanut butter and jelly sandwiches every day for two weeks.

“It’s the grittiness of it.”

That part of Round Top rarely makes the polished photo, but it is often what makes the finished booth possible.

Derek is the dreamer. Jill, he says, is the practical one. The perfect pair!

“She basically works for Saints for free.”

She has been beside him through the mountaintops and valleys of building the business, while also helping Derek recognize when trying to carry everything himself is no longer sustainable.

“I couldn’t do this without her.”

And then there are the other vendors.

“Everybody’s out there just grinding.”

Derek talks about the community around him at the Arbors, including Curtis Ann and the vendors he has worked alongside, as one of the things he has come to love about Round Top.

“It’s not a competition to us. It’s more like, hey, all ships rise when we celebrate and help one another.”

Derek still speaks about Saints with the posture he had when the whole thing was much smaller.

“I’m holding it with loose hands.”

A hat he first wore because he did not want to be seen became something he learned to make. Making them brought him Clint Hough which then brought him to Round Top. An Airstream found at the Arbors eventually went on tour.

And the pastor who once dreamed of making a hat for Brandon Lake ultimately found a business partner and then in Nashville making hats for some of the biggest names in music.

The story is still being written.

And when the dream he once thought was big enough came true? Derek's story and friend reminds us, you've got to dream bigger.

“Well, you better dream bigger because God did that, you know, in a few months.”