Tom Jackson’s journey into the outdoor advertising industry is one of perseverance, adaptability, and a deep understanding of the value billboards bring to local communities. As the owner of a billboard company in Northern California, Tom’s story exemplifies the entrepreneurial spirit and the tenacity needed to succeed in a competitive and evolving market.
A Unique Path to Billboards
Tom’s career didn’t start in outdoor advertising—it began in the U.S. Army Military Police Corps. After his service, Tom transitioned into managing commercial real estate for his former father-in-law, Kirk Veal, who also owned a handful of billboards. By 1991, Tom found himself managing the billboard side of the business after the previous manager was elected to Congress.
Tom’s early days in billboards were marked by innovative strategies. “We used to buy land with existing billboards and convert them to our ownership,” Tom recalled. “It was old school, but it worked.” In one memorable instance, Tom even slept in a van under a billboard to prevent it from being cut down during a legal dispute. That grit paid off when his team won a landmark court case, securing their assets and paving the way for future growth.
Building a Modern Legacy
For nearly two decades, the billboard business remained a small but steady component of the operation. However, during the 2008 recession, Tom saw an opportunity to expand. He and Kirk pivoted, acquiring underperforming digital billboards and successfully bidding on new projects.
“We beat Clear Channel and Outfront for a digital in Sonoma County,” Tom shared. “It was a game-changer for us.” Today, Tom’s company operates a mix of static and digital billboards, with digital faces contributing significantly to the company’s revenue.
Tom took full ownership of the company in March 2022 after Kirk’s passing, transitioning from a hands-on general manager to owner and strategist. “My role has shifted,” he explained. “I still handle legacy accounts, but now I focus on growth opportunities, developing new sites, and managing the team.”
Resilience Through Challenges
Operating in California comes with unique hurdles, from stringent regulations to fierce competition. Tom’s advice for new operators reflects the lessons he’s learned:
- Have a Good Attorney: “In California, legal expertise is essential to navigate the complexities of billboard permitting.”
- Be Patient: “Billboards aren’t quick wins. It takes time to find the right locations and work through approvals.”
- Do Your Research: “Understand local codes, ordinances, and the competitive landscape. It’s a lot of reading, but it’s crucial.”
Finding Joy in the Work
When asked what he enjoys most about the business, Tom’s passion is evident. “I love finding new locations and working with clients to create campaigns that drive results,” he said. “There’s nothing more satisfying than seeing a client succeed because of a well-placed billboard.”
Tom also values long-term relationships with clients, many of whom have been with his company for decades. “We’ve had some clients for over 20 years,” he noted. “It’s rewarding to know we’re part of their continued success.”
Looking Ahead
As Tom eyes the future, he’s focused on leveraging technology to optimize operations and exploring opportunities for digital expansion. “We’re a small team, but we’re resourceful,” he said. “I’m working on bringing in an intern to help us fully utilize the tools we have, like Quantum and GeoPath, to their fullest potential.”
Tom’s journey from managing a few billboards to owning a thriving outdoor advertising business is a testament to resilience, creativity, and a deep understanding of his market. His story is an inspiration to independent operators and a reminder of the incredible opportunities that lie in outdoor advertising.