An entrepreneur builds a multi–company legacy through discipline, community roots, and steady expansion in Williamson County.
John Montgomery still remembers the feeling of standing in a small print shop in Georgetown, Texas, wondering whether hard work alone would be enough. It was 2004. The risk felt real. The outcome uncertain. Like a long night at the poker table, the decision required patience, discipline, and the confidence to play the hand he had been dealt.
Montgomery had recently left Emporia, Kansas, where he was raised by a single mother who worked long shifts at the Dolly Madison factory. Together, mother and son took a leap and purchased a local business called Roberts Printing. There was no safety net—only faith in effort, relationships, and the belief that steady, ethical work would eventually pay off.
That moment marked the beginning of a Georgetown, Texas, entrepreneur story that continues to shape Williamson County today. Now a CEO overseeing multiple companies, Montgomery has spent more than two decades building businesses that grow with the community rather than chasing trends. His journey mirrors the rapid expansion of the Austin metro area while remaining grounded in small-town values, Midwest discipline, and a mindset sharpened by years of strategic thinking—both in business and at the poker table.
From One Print Shop To A Purpose Driven Mission
Roberts Printing was not a flashy acquisition. It was a working class operation with loyal customers and modest margins. Montgomery learned quickly that survival required consistency and trust. He focused on quality, responsiveness, and relationships. Those principles became the foundation of Roberts Printing in Georgetown Texas, a company that has since earned Georgetown’s Best Printing Services Gold for ten consecutive years.
In 2015, another turning point arrived. Montgomery’s mother retired, and he purchased her shares of the business. The transition was personal and symbolic. It marked the shift from a family supported venture to a company fully under his leadership. “My mom taught me what work ethic really looks like,” Montgomery has said in past conversations. “Everything I do in business still reflects that example.”
Recognition followed. Roberts Printing received the Georgetown Chamber Small Business of the Year award in 2018, and Montgomery earned Alignable Small Business Person of the Year honors in back to back years. These accolades were not marketing stunts. They reflected years of steady service and deep involvement in the local business ecosystem.
Playing the Long Game in a Fast-Growing County
Montgomery’s philosophy favors long games over quick wins—an outlook shaped in part by his passion for poker. An avid player, he approaches business much like the game itself: manage risk, read the table, and never overextend chasing a short-term payoff. That mindset has served him well as Williamson County has become one of the fastest-growing regions in the country.
His involvement with Business Networking International (BNI) spans more than fifteen years, reinforcing his belief that sustainable growth comes from trusted relationships, not speculation. While others chased rapid expansion, Montgomery invested in infrastructure, people, and capabilities that would endure.
In 2022, he acquired D&L Printing, expanding production capacity and technical expertise. In late 2025, he co-founded Branding Bros with partner Cole Vanelli, launching an apparel branding company designed to help businesses build cohesive, professional visual identities. Most recently, Montgomery partnered with Larry Davis of L&R Signs to acquire Georgetown Sign Company, bringing full in-house commercial sign fabrication into his portfolio. Most sign companies out-source all of their sign fabrication. This also allows them to create relationships with other sign companies by offering them wholesale sign fabrication.
This acquisition marked a strategic breakthrough. By bringing sign fabrication under one roof, Montgomery positioned his companies to offer end to end branding solutions. Businesses can now move from concept to print to signage without leaving Georgetown. This integration sets his group apart from competitors who rely on outsourced production.
What Makes His Companies Different Today
All four companies are based in Georgetown, Texas, and all share a common operating philosophy. Control quality. Invest locally. Give back consistently. With Georgetown Sign Company now part of the group, Montgomery’s operations provide comprehensive branding and printing services that scale with client needs.
Equally important is his commitment to community involvement. Montgomery and his businesses are known for supporting local causes, assisting small businesses in need, and stepping up during difficult times. This approach has strengthened loyalty and reinforced trust, two assets that cannot be replicated by national chains.
Behind the titles and acquisitions is a single father raising his sixteen year old son, Preston. Montgomery speaks openly about balancing leadership and parenthood. That balance influences how he leads teams and chooses opportunities. Growth, for him, must support life, not consume it.
A Georgetown Texas Entrepreneur Investing In The Future
Montgomery also owns nine additional companies in non related industries, a detail that underscores his versatility as an entrepreneur. Yet his heart remains in Williamson County. As the region grows, he continues to invest in businesses that serve its expanding population and support fellow entrepreneurs.
For readers following business leadership stories on CEOTimes.com, Montgomery’s journey offers a grounded example of how expansion can be intentional rather than reckless. His success did not come from chasing headlines. It came from mastering fundamentals and staying present in the community he serves.
Businesses seeking reliable printing, signage, or apparel branding solutions can explore Roberts Printing, learn more about full service signage at https://georgetownsign.com, discover custom apparel at https://brandingbrostx.com, or review expanded print capabilities at https://dlprint.com. Each site reflects the same promise that started in a small shop in 2004: show up, deliver quality, and build something that lasts.
As Williamson County continues its rapid rise, John Montgomery remains focused on steady growth, local partnerships, and creating businesses that reflect the people they serve. His story is not about luck or shortcuts. It is about commitment, discipline, and believing that long term value still matters.
