If you drive east of Boerne, where the land begins to rise and the trees crowd closer to the road, you’ll see a stretch of fence that tells you exactly who lives there. Simple white signs with bold red letters, speaking the kind of truths that make people honk, grin, and nod their heads. They belong to Donald “Donny” May, a man who has never been afraid to stand for what he believes in.
Those signs aren’t for attention. They’re for expression. “They’re my only voice,” Donny says. “I put them out there for folks who think like I do but don’t have a platform. It lets them vent a little. Maybe they honk, maybe they smile, and maybe they go home feeling a tiny bit better. They’re not alone.”
That’s the kind of man Donny is. A quiet leader. A hard worker. A man who has built more than businesses. He has built a legacy rooted in faith, family, and a love for Kendall County that runs as deep as the limestone beneath it.
Raised on Faith and Grit
Donny’s story begins with two people who shaped him more than anyone else. “My dad, Donald Sr., was raised during the worst of the Depression,” he says. “He grew up in Kingsville in a big Catholic family of sharecroppers. They were extremely poor. At sixteen, he got his pilot’s license by working odd jobs at the airport. At eighteen, he joined the Air Force and served in the Pacific during the Korean conflict.”
His father’s love of flying took root in him, too. “He passed that into my genes,” Donny says. “I became a pilot in my thirties. I still love to fly. He was a great Christian man in every sense of the word.”
Donny’s mother is just as important to his story. “Mom is a strong Baptist. She made sure we were in church every Sunday at Castle Hills Baptist. She was a stay-at-home mom, but she spent her days volunteering for CASA, helping rescue abused children. She’s still alive, still sharp, and still the same strong woman she has always been.”
He pauses before adding, “I was fortunate to have such great Christian parents.”
He also speaks with affection about his siblings. “I still have one sister, Sherri, and my little brother Gary. We all get along great. Gary’s the kind of guy who’d literally give anyone the shirt off his back. I am so blessed.”
Those lessons of faith, family, and grit stayed with him. They formed the foundation of every business and every decision that would follow.
The Years That Shaped Him
After graduating from Marshall High, Donny attended UTSA. “I graduated in 1981 with a business degree in accounting,” he says. “That was the worst year to enter the workforce because we were coming off the Jimmy Carter depression. I got a job as a ditch digger and fuel system worker with my wife’s uncle. Anything to put food on the table.”
That job might have looked humble, but it became the starting point for something extraordinary.
“I’ll never forget the day it all changed,” he says. “I was digging a ditch by hand in downtown San Antonio, uncovering a buried fuel tank. I stood up in the hole, my head just sticking above ground. I saw four sets of shiny shoes with men in suits holding briefcases. They were the guys I’d graduated with from UTSA, all of us accounting majors. They started laughing. They were belly laughing at me. It was the insult I needed. That was the spark. I wanted to cover myself up in that hole and disappear, but instead, I decided right there that it was time to start my own company. That was divine intervention.”
That day in the dirt changed everything.
Building from the Ground Up
Donny had always been an entrepreneur. “When I was nine, I had a mowing service,” he says. “I opened an account with E.F. Hutton and met with my broker every month to talk about investments. I’d ride my bike to the library to read up on different companies. I didn’t make much because commissions ate up most of it, but I learned the system.”
That curiosity turned into innovation. With his background in accounting and hands-on field work, Donny began to see how fuel systems could be improved. “My uncle-in-law had a company that installed underground fuel systems. I was making five dollars an hour, but with my math background, I started developing more sophisticated leak detection methods. Eventually, Tami and I started our own company performing precision leak testing.”
In those days, there were no environmental regulations. “Back then, you only fixed leaks if they hurt your profits,” he says. “We wanted to do it right. We wanted to stop the leaks before they ruined anything.”
They were good. In fact, they were the best. “Shamrock was a fledgling company then,” he says. “They recognized the value of finding and preventing leaks. They used us exclusively and really put us on the map.”
That success led to bigger opportunities. “Because of our database of testing results, the EPA contracted me to help determine how many leaks existed and how bad they were. That became the sole study the EPA used to write the regulations for underground fuel systems. It was a game changer.”
As the industry evolved, Donny saw a new opportunity. “After that, I decided to step into cleanup. I formed a drilling company to help engineers install systems to capture the liquid hydrocarbons leaking into our drinking water. It required knowledge, licensing, safety training, and specialized equipment. The barrier to entry was high, but that’s why we excelled. We covered most of the market.”
He smiles when he talks about the men who worked for him. “We gave every single client our best effort. Our motto was simple: good enough is not good enough. After thousands of projects, we never had a major injury or accident. We cleaned up countless spills that were headed into aquifers. One of our biggest local jobs was drilling around Kelly and Lackland. My crews worked in space suits with supplied air. Thank God we were able to give those homeowners their lives back.”
He leans back for a moment. “In retrospect, if I’ve done anything for the betterment of the community, it’s that we prevented an unknown number of contaminated aquifers and fixed others that were already ruined. That’s something I’m proud of.”
Eventually, he sold the company, now part of Alamo1. “It was God’s company,” he says. “That’s why it was protected and successful.”
The Woman Who Made It Possible
Every story of success has a backbone, and in Donny’s case, it’s his wife Tami.
“She was divine intervention,” he says quietly. “She was the shadow force that kept everything together. She is so smart, so hard-working. Without her, our companies would have failed. I got the credit because I was the front man, but I know the truth. Without her, I’d still be operating a shovel.”
When their first company went public, the auditors from Ernst and Young were stunned. “They told us it was the best small company they’d ever audited,” he says. “Everything was perfect. That was all Tami. I married a beautiful blonde, thinking she was just cute. Turns out she’s an accounting genius.”
Together, they raised two children who share their parents’ work ethic. “Kristin and her husband Jeremy run Kendall Point,” he says proudly. “Jonathan owns Mayday Investigations. Both are entrepreneurs, just like their mom and dad. We’ve got five grandkids, from four months old to sixteen. They’re all blessings.”
Faith and Fortitude
Donny’s success didn’t come without resistance. “We’ve been harassed by agencies for years,” he says. “Federal, state, local, you name it. I believe it’s because we fight for what’s right. We never give up, and we realize freedom isn’t free. The day you give in to government bureaucracies, you become part of the problem. That will never happen in the May family.”
His signs along Highway 3351 are part of that same conviction. “They give people hope,” he says. “Hope that they’re not the only ones who feel this way.” He laughs when he talks about the times pilots have called him from above. “I’ve even plowed messages into my hayfields. You can see them on Google Earth. One pilot friend told me he flew over my field, and the whole plane started guffawing. I guess I made a few snowflakes melt that day.”
For all his toughness, Donny’s words always circle back to gratitude. “Always include God in every venture,” he says. “Be honest and fair. Give more than you promise. Take care of your employees because they are the company. And never, ever, ever give up.”
He looks out toward the ranch, quiet for a long moment. “I’ve fought a lot of battles in life. Some I won, some I didn’t. But I’ve learned that being scared is okay. Being too scared is not. You fight, and you keep fighting, because the minute you quit, you lose everything.”
A Ranch and a Legacy
The May ranch in Bergheim sits on land that tells its own story. “Some of these structures go back to the 1880s,” Donny says. “You can still find pieces of wagon wheels, old tools, remnants of what came before us. I’ve tried to buy back the pieces as other ranchers sold off. Too many people are losing their land. I want to keep this place together.”
He loves Kendall County for what it is. “Be thankful for what you have,” he says. “Be thankful you live in Kendall County. Don’t let people modernize it. Keep it the way it is.”
He smiles as the wind shifts through the pasture. “I’ve tried to build something that lasts longer than me. Between the ranch, my family, and the people we’ve helped, I think we did that.”
The Measure of a Man
I’ve known the May family nearly my whole life. Donny’s son, Jonathan, has been my best friend since first grade. Donny has always been like a second dad to me. After my father passed away, he pulled me aside after the funeral and said, “I’m Dad now.” He didn’t mean it as a replacement, but as a promise that I’d always have someone to turn to for wisdom, advice, and strength.
My dad and Donny used to talk about “their boys.” They took pride in the way we grew up, worked, and found our own paths. When I started The Kendall Gentleman, I knew I’d write this story someday. I just needed to wait for the right moment.
Today feels like that moment.
Donny May has spent a lifetime building, teaching, and standing firm. He has fought for his family, his faith, and the land he loves. He has given more than he’s taken, believed more than he’s doubted, and worked harder than most ever will.
He’s a husband, a father, a mentor, a patriot, and a man who never quits. Around here, that’s the highest kind of compliment.
He never set out to be recognized, only to do what was right. But when you measure a man by his faith, his work, and the legacy he leaves behind, you find what this magazine was created to celebrate. I’ve known Donny most of my life, and I can tell you this with certainty: if the pages of this magazine were meant to honor men of integrity, grit, and grace, then they were meant for him.
For those reasons and many more, Donny May is The Kendall Gentleman.
More from The Kendall Gentleman: for another man whose character was revealed in what he refused to quit on, read Find a Way: The Making of Jordan Ballin. And for the quieter version of the same conviction, Bill Whitworth and the Quiet Work That Holds a County Together shows what it looks like without the headlines.
