Few individuals embody the principles of The Kendall Gentleman as fully as Tommy Mathews. His life story, deeply rooted in the traditions of Kendall County, reflects a balance of leadership, integrity, faith, and an unwavering commitment to his community. From his early days exploring the Hill Country to his current role as a businessman, mentor, and family man, Tommy exemplifies the timeless principles we celebrate in every issue of this magazine.
Rooted in Kendall County
Tommy Mathews’ journey began in San Antonio, but it wasn’t until his family moved to Boerne in 1967 that his deep connection to Kendall County truly took shape. At the age of seven, Tommy discovered the freedom and simplicity of rural life. “I always wanted to live in the country,” he recalls. Boerne offered just that, with a tight-knit community, rolling hills, and a lifestyle where kids could ride bikes everywhere and neighbors were like family.
Family was foundational to Tommy’s upbringing. His mother, a stay-at-home mom who later became an educator and served nearly 20 years on the school board, inspired him with her dedication to service. “Her commitment to education and the community left a huge impression on me,” he shares.
Tommy’s father also played a pivotal role in shaping his character. A hard-working man who climbed the ranks in the concrete industry, he instilled in Tommy a love for the outdoors and a strong sense of resilience. “Dad could always connect life lessons to football,” Tommy recalls, reflecting on the values of discipline and teamwork that his father’s wisdom imparted. He adds, “My father taught me that no matter what life throws at you, integrity and perseverance will see you through.”
Those early years also included unforgettable memories of events like Berges Fest, a cherished tradition that introduced Tommy to the vibrant culture of Kendall County. These experiences laid the groundwork for the values he would carry throughout his life.
A Leader from the Start
Tommy’s leadership qualities emerged early. At Boerne High School, he excelled both academically and athletically, graduating in 1978. He served as student body president, co-captain of the National Honor Society, and was a standout on the football team, wearing #75 with pride. “Football taught me more than just how to play the game—it taught me how to face adversity and keep pushing forward,” Tommy explains.
Key mentors during this time, like Coach Diz Reeves and local leader Edgar Schwarz, played pivotal roles in shaping Tommy’s character. “Coach Reeves was tough, but he made you proud of where you came from,” he says. These influences instilled in Tommy a sense of pride in his community and a drive to give back.
In addition to excelling in academics and sports, Tommy’s high school years were marked by his founding role in the Fellowship of Christian Athletes (FCA). Inspired by figures like Obert Logan and Tom Landry, Tommy began to develop his philosophy of servant leadership—a principle that would guide him throughout his life. “Faith has always been a cornerstone of my life,” Tommy says. “FCA helped me see how faith and leadership go hand in hand.”
Building a Career and a Community
Tommy’s path after high school led him to Trinity University, where he graduated in 1982 with a degree in geology. The downturn in the oil industry soon after graduation forced him to pivot, leading to a career in construction. It was in this field that Tommy discovered his entrepreneurial spirit, eventually founding Westward Environmental in 1996.
“Starting Westward was a leap of faith,” he admits, crediting prayer and inspiration from the hymn “We Three Kings” for guiding his decision. Today, Westward Environmental is recognized for its innovative solutions and commitment to ethical practices. “It’s not about whether we need something; it’s about how we approach it responsibly and with care for the community,” Tommy explains.
Throughout his career, Tommy has drawn heavily from the teachings of Dr. Stephen Covey, whose book First Things First became a guiding framework. “Dr. Covey taught me the importance of living by principles and understanding the difference between what’s urgent and what’s important,” Tommy says. “Those lessons have shaped how I approach both my work and my personal life.”
His career has been marked by moments that tested his principles, including instances of confronting unethical behavior and helping clients through difficult challenges. Through it all, Tommy has remained steadfast in his commitment to integrity and doing what’s right.
A Life of Service
Beyond his professional achievements, Tommy’s contributions to Kendall County are a testament to his dedication to service. He has been actively involved in numerous local organizations, including Boerne ISD athletics, the Cow Creek Groundwater Conservation District, and St. Helena’s Episcopal Church, among others. “It’s exciting to support organizations and events that make Boerne special,” he says.
Service is more than a commitment for Tommy; it’s a way of life. He mentors young athletes through FCA, emphasizing the importance of faith, discipline, and perseverance. “You’re either a giver or a taker,” he states firmly. “I choose to be a giver.” Since I met him more than a decade ago, Tommy has been a constant source of mentorship and friendship.
Balancing Work, Family, and Legacy
Despite his busy schedule, Tommy prioritizes his family and cherishes the moments spent together. He works alongside his sons at Tusculum Brewing Company and Westward Environmental, blending his passion for community with his commitment to family. “There’s nothing better than working with my boys and seeing their passion for what they do,” he says.
Tommy’s wife, Dana, has been his partner and support system throughout their journey together. The two met at a Trinity University football game and have built a life rooted in love, faith, and shared values. “Dana has always been my rock,” Tommy says. “She’s the foundation of our family.”
When not working or volunteering, Tommy enjoys the natural beauty of Kendall County, whether fishing on the Guadalupe River or enjoying the incredible sunsets with Dana. These moments in the great outdoors provide him with the space to reflect on his life and the legacy he hopes to leave behind.
Wisdom for the Next Generation
Tommy’s advice to younger generations is simple but profound: “Get involved. Be a servant leader. Use your time and talents to make a difference in your community.” He also stresses the importance of civic engagement, emphasizing, “If you don’t vote, you don’t have a say. It’s that simple.”
His guiding principles—integrity, loyalty, and trustworthiness—are constants in his life. “Values may change, but principles don’t. They’re what keep us grounded,” Tommy explains. Little did he know, it was this very sentiment that was the final spark that ignited The Kendall Gentleman. Standing outside Tusculum Brewing, Tommy explained to me the lesson he teaches his employees about the difference between principles and values. “Values change with the time and with social mores. Take for example: people used to value taking the time to sit down and write a letter to someone. Not so much these days – but that’s ok!” he elaborated. “Principles, however, like integrity, loyalty, and trustworthiness – those remain unchanged, said Tommy.”
The Spirit of Kendall County
Tommy Mathews exemplifies everything The Kendall Gentleman stands for: a commitment to tradition, a dedication to service, and an unwavering love for Kendall County. His life is a testament to the enduring qualities of a true gentleman, from his principled leadership to his passion for family, church, and community.
As I launch this magazine, Tommy’s story reminds us all of the values that make Kendall County unique. He challenges us to lead with integrity, give back more than we take, live a Christ-centered life, and preserve the legacy of this remarkable place we call home. It is an honor to feature him as the inaugural Kendall Gentleman.
