Wes Holekamp: The Long Road Home

Wes Holekamp left Comfort to build a career. Years later, he came home to raise his family in the same Hill Country community that raised him, and found there was still work to be done.

There are a lot of ways to measure the distance between Comfort and Fort Worth. On a map, it is a little more than 250 miles. For Wes Holekamp, there was a stretch of life when that distance became something much more personal.

“I was coming from Comfort to Fort Worth every week for six months,” he said. “That’s like two hundred fifty-six miles one way.”

Then, with the kind of understatement common among men who have already decided something simply has to be done, he added, “It was a little bit of a chore to manage family life and getting to things, but we made it work.”

That drive gets close to the heart of Wes’s story. He spent years building a life somewhere else, then reached a point when home began pulling harder than opportunity was pushing.

Wes grew up on Cypress Creek, the only child of Glenn and Edith Holekamp, in a family whose name has been part of Comfort for generations.

“We were born and raised here in Comfort, out in the Cypress Creek area,” he said. “Both my parents were born and raised here.”

After graduating from Comfort High School in 1998, Wes headed to Tarleton State University, where he studied Agriculture Services and Development. The degree generally pointed students toward agricultural education or Extension work, but Tarleton exposed him to a different world.

“Once I got a little bit of a taste of the corporate world, which I wasn’t exposed to here growing up, I thought that might be something worth expanding my horizons on,” he said.

So he added marketing and business classes. He also met Brandy, the woman who would become his wife.

“I stumbled on the love of my life,” he said.

After college, the couple settled in Fort Worth, where Wes went to work for Ag Workers Insurance. He began in marketing and eventually became director of marketing. The job put him on the road constantly, traveling across Texas and working agricultural conferences, meetings, and events.

“I really enjoyed getting out and meeting with folks,” he said. “I enjoyed the time on the road, but I didn’t enjoy being away from my family.”

Once children came along, that mattered more.

“It wasn’t unheard of for me to drive from Fort Worth to San Antonio for an evening meeting and then back again,” he said. “So that can make for a very long day.”

Wes stayed with Ag Workers for about 12 years. Then the company went through a reduction in force, and he was one of several employees let go.

There is no bitterness in the way he tells it now.

“One of the things I learned from that is that something that was probably hurtful at the moment opened my eyes,” he said. “It made me expand my reach, wanting to see what else was out there.”

That led him to Great American Insurance Group and to a specialty line of insurance dealing with theft, fraud, embezzlement, and other financial crimes.

What Wes likes about the work is that it still requires judgment.

“A lot of the P&C lines, especially, become so automated,” he said. “You put in a driver’s license number or a VIN number, and it spits out a number.”

His side of the business is different.

“We get to set the price and the deductible. We get to put the forms and endorsements,” he said. “We get to build a deal. Get to make a deal.”

There is something fitting about that. A fifth-generation Hill Country man working in a modern corporate world, but still drawn to work where relationships, judgment, and experience matter.

Great American also became important to Wes when his mother became ill. His manager gave him the flexibility to work remotely so he could spend more time in Comfort helping her.

“I felt very loyal to the company for allowing me to do that,” he said.

His father had already passed away. When Edith later died, Wes was an only child, and the family home place remained.

That forced a conversation.

“We said maybe it’s time to move back,” he recalled. “I think the kids will thrive in a smaller community, and so we made the move.”

They put their Fort Worth house on the market and expected the process to take a while.

It sold in four days.

After finishing out the school year, the family headed south and moved into the same Cypress Creek house where Wes had grown up. The place needed work, and the renovation meant spending about six months in a travel trailer.

Still, Wes never questioned what the move meant.

“For me, it felt like I was coming home,” he said. “I knew we would have a network, so to speak, of support here.”

“For me, it felt like I was coming home. I knew we would have a network, so to speak, of support here.”

That move also put his children into the same community that had shaped him. Kayleigh has now followed him to Tarleton, while Mason has started his freshman year at Comfort High School.

“I’m fifth generation, so my son Mason is the sixth,” Wes said.

His grandfather attended the old Cypress Creek schoolhouse before the rural schools were consolidated into larger districts. The Holekamp name itself reaches deep into Comfort history, and Wes still keeps an original 1856 family land deed.

The age of the family name occasionally produces some humor too.

At a Boys & Girls Club fundraiser, a couple who had purchased an old Holekamp house was excited to meet him after researching the property and walking through the cemetery.

“She said honestly, this is the first live one.”

Since coming home, Wes has steadily found himself pulled into community service. He first became involved with the Cypress Creek Community School organization, where the need was pretty simple.

“They were just looking for young folks to help, mow and keep the place up,” he said.

That eventually led to other roles, including service with the Kerr Central Appraisal District, the Comfort Cemetery board, and multiple years as a deacon at First Baptist Church in Fredericksburg.

Then somebody asked him to run for the Comfort ISD Board of Trustees.

Wes had already been attending meetings and paying attention to what was happening in the district. When the trustee representing his area decided not to run again, he approached Wes.

“I thought, that’s the gift that keeps on giving,” Wes said.

He filed anyway. No one ran against him, and not long after he joined the board, the district entered what he described as a “hornet’s nest” of issues.

Wes says he did not run with a personnel agenda.

“I had run my campaign on transparency, and I wanted more flow of information from the district down to the community,” he said. “I was not there with an agenda to hire or fire somebody.”

One piece of advice from another trustee has stayed with him.

“When you’re making decisions, make sure it’s to the benefit of the kid,” he said. “Then you know you’re making the right one.”

You can see that philosophy most clearly in the way he talks about career and technical education.

Comfort ISD has expanded welding and other workforce-oriented programs. Mason recently earned a welding certification before even beginning his freshman year.

At home, Wes sees both sides of the education debate.

“I’ve got one that was ready to go to college, and I’ve got one that is not wanting to go to college,” he said. “Which is fine. We have to be able to do both.”

That may be one of the simplest summaries of good education policy you will hear. A school should not manufacture identical futures. It should help young people build useful ones.

Late in our conversation, I asked Wes what advice he would give the men of Kendall County.

His first answer was service.

“Find something in the community that you can be active in, participate in, and give a hundred and ten percent,” he said. “Don’t give fifty; give a hundred and ten.”

Then he talked about faithfulness.

“Be faithful to your wife,” he said, before broadening the thought. “Faithful not only to your spouse, but to your family, to your kids, to your money, to your school, to your church.”

Faithfulness is a pretty good word for Wes’s story. Faithful to Brandy, whom he met at Tarleton. Faithful to Kayleigh and Mason, whose futures changed the way he thought about work. Faithful to a company that gave him room to care for his mother. Faithful enough to come home, and faithful enough to stay involved once he got here.

When I asked what advice he would give younger men, his answer came back to relationships.

“Build relationships, both older and younger than yourself,” he said. “Not online. In person.”

That tracks with the way he has built his career, his public service, and his life in Comfort.

These days, Wes admits there is not much spare time left over for hobbies. He likes to fish, travel with Brandy, and spend time in the deer blind with Mason.

“I enjoy going with my son now,” he said. “So I mostly just sit there and pester him.”

For a man whose professional work stretches far beyond Comfort, his world has become remarkably local again. The old home place, Brandy, Kayleigh and Mason, a school district, a cemetery, a community and a family name that was here long before him.

So I asked him what keeps him going.

“The kids do,” he said. “The kids keep me going. Not just mine, but all of them.”

Maybe that is what the long road home was really leading toward. Wes Holekamp went away from Comfort to build a life, and he came back to help build what comes next.

For that, we are proud to recognize Wes Holekamp as The Kendall Gentleman.

From the October 2026 issue of The Kendall Gentleman.

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Wes Holekamp’s family history is explored further in this issue’s History feature, The Holekamps: A Family That Helped Build Kendall County, and this month’s Publisher’s Note, Faithful in the Small Things, reflects further on his story. For more cover stories on Kendall County legacy families, read The Man Who Built Joy.