When Randy Oliver joined his father-in-law Doyle Benton’s garage door company in 1981, he wasn’t setting out to build a decades-long legacy. He was a 21-year-old, newly married college student learning the business from the ground up. More than 40 years later, that decision has shaped not only his career but a family-owned company that has grown alongside San Antonio’s booming housing market.
Oliver’s entry into the industry was hands-on from day one at Hollywood-Crawford Garage Doors and Openers. He began installing garage doors, learning the mechanics and demands of the trade before moving into sales, management and eventually company leadership. What started as a small operation with about 20 employees has grown into a regional business with more than 70 team members serving San Antonio and surrounding communities, including New Braunfels.
The company’s roots stretch even further back. Founded after World War II by Harry Crosland, the Hollywood Crawford brand expanded across Texas through independently owned, family-run businesses. That legacy of craftsmanship and independence remains central to Oliver’s approach today.
Among the accomplishments Oliver is most proud of is his long-term service to the industry. He served 13 years on the board of the International Door Association, including two years as president, helping guide standards and build relationships across the United States and Canada. Locally, he has remained active with the Greater San Antonio Builders Association and the Greater New Braunfels Home Builders Association, partnering closely with builders as the region continues to grow.
Within the company, one of the most meaningful milestones is succession. Today, Oliver’s two sons, Chris and Jonathan, hold key leadership roles. Chris oversees daily operations, while Jonathan manages sales, ensuring the business remains family-owned while preparing for the future.
Like the real estate industry itself, Oliver’s career has weathered multiple cycles. The late 1980s were particularly challenging, with housing starts in San Antonio dropping to historic lows. Rather than retreat, the company diversified its services to keep employees working and weather the downturn.
During the 2008-09 housing crisis, a strategic partnership with a national manufacturer helped the company grow market share even as others contracted. The experience reinforced a lesson Oliver still carries: adaptability, relationships and long-term thinking matter more than short-term trends.
At Hollywood-Crawford Garage Doors and Openers, community involvement is a core value. Over the years, Oliver and his team have supported numerous local and regional organizations, including Daily Bread Ministries, One Hope for Kids, South Texas Alliance for Orphans and the S.H.A.R.E. Center, a crisis pregnancy resource in the Spring Branch area.
The company also encourages hands-on service. Leadership and sales teams have volunteered with local nonprofit organizations, reinforcing a culture that values contribution as much as performance.
One trend Oliver continues to highlight is the growing recognition of garage doors as a high-impact home improvement. According to Remodeling magazine’s Cost vs. Value report, garage door replacement consistently ranks among the top projects nationwide for return on investment, often outperforming more expensive renovations.
For newcomers to real estate or homebuilding, Oliver’s advice is practical: Pay attention to details that shape first impressions and functionality. A garage door can account for a significant portion of a home’s front elevation and is one of the most frequently used moving components in a house. Regular maintenance and thoughtful design choices can prevent costly breakdowns and add measurable value.
Outside of work, Oliver values time with family above all else. He enjoys traveling with his wife and family and has maintained a weekly basketball game since his teenage years. Today, he is joined by his sons, son-in-law and grandson — a routine that mirrors his professional life: consistency, relationships and staying active.
Whether working with national builders, custom home projects or homeowners preparing to sell, Oliver’s message is simple: Small details can make a big difference. From curb appeal to daily functionality, the right garage door — and the right partner — can add lasting value.
