Member Spotlight: Veale Outdoor Advertising

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One of my favorite parts of this role is getting to slow down and really listen to our members’ stories. Not just how many boards they have or where they’re located-but how they got here and what they’ve learned along the way. That’s exactly what made this conversation with Tom Jackson so special. Tom’s journey is a reminder that most independent billboard businesses aren’t built overnight-they’re built over decades, through relationships, resilience, and a whole lot of persistence.

From the Army to the Industry

Tom’s path into billboards wasn’t something he set out to do. After serving in the U.S. Army Military Police Corps and spending time overseas, life brought him back stateside, eventually landing him in California. In 1988, he joined his father-in-law’s business, which at the time included car dealerships, real estate, and just a handful of billboards. His role focused on managing commercial and residential real estate-no car sales, no billboard sales, just learning the business from the inside out.

That changed in the early ’90s when the person overseeing the billboards left for Congress. Tom stepped in to manage the billboard side of the operation, and what started as a small responsibility quickly became a defining part of his career.

Learning the Billboard Business the Hard Way

Like many independent operators, Tom didn’t inherit a polished playbook or formal training. He learned by doing. In the early days, growth came through owning land beneath existing billboards and navigating the rules-sometimes creatively, always persistently. There were legal battles, tense moments, and even nights when Tom slept in a van under a billboard to make sure it wasn’t taken down during a dispute.

Those experiences weren’t just dramatic stories-they were formative lessons. They taught him how important it is to understand local regulations, protect your assets, and stand your ground when you know you’re right. It’s the kind of hands-on education that can’t be taught in a classroom.

A Steady Business Built on Relationships

For many years, the billboard side of the business stayed intentionally small and steady. The boards were full, relationships were strong, and there was no rush to chase growth just for growth’s sake. That long-term mindset is still reflected today. Tom has clients who have been on the same boards for 20-and even 30-years. That kind of loyalty doesn’t happen by accident.

What keeps those relationships strong is Tom’s approach to selling. He’s not interested in one-off deals that don’t work. He enjoys collaborating with advertisers, helping them think through location, message, and strategy so the billboard actually drives results. When a campaign works, everyone wins-and that’s the part of the business he enjoys most.

Leaning Into Digital—Thoughtfully

Like many operators, Tom eventually leaned further into digital during changing market conditions. Some opportunities came through competitive bids with cities, where strong proposals and local relationships made all the difference. In each case, the focus stayed the same: be a good partner, support community messaging, and make sure the arrangement works for both sides.

At the same time, Tom is clear-eyed about digital saturation and market differences. What performs well in one corridor may not work the same way in another. That practical, experience-based perspective is something many independents can relate to-and learn from.

The Realities of Being a Small Operator

Tom doesn’t shy away from talking about challenges. Technology costs, reporting requirements, and industry tools can feel overwhelming when you’re running a lean operation with just a few people wearing many hats. While large companies may have entire departments dedicated to data, IT, and analytics, small operators are often juggling sales, operations, invoicing, and compliance all at once.

Even so, Tom stays focused on what matters most to his advertisers-location, visibility, and results. Most of his local and regional clients don’t ask for complicated metrics. They want to know how close the board is to their business, whether it’s the last sign before an exit, and if it’s helping drive customers through the door.

Advice for the Next Generation

When asked what advice he’d give someone new to the industry, Tom’s answer was thoughtful and honest. Do things legally. Be patient. Read everything-ordinances, codes, general plans. If you can, work for a larger company first and learn how the business operates at scale. And most importantly, talk to other operators. Ask questions. Learn from their mistakes as well as their successes.

That willingness to share knowledge is exactly what makes this community special.

Why Community Matters

Throughout our conversation, one thing was clear: Tom values relationships-within his business, with his advertisers, and across the industry. Organizations like IBO, state associations, and industry peers have played a meaningful role in helping him navigate challenges and make informed decisions. And just as important, Tom continues to pay that support forward by helping others who are just getting started.

Stories like Tom’s are why we do what we do at IBO. They remind us that independent operators are resilient, resourceful, and deeply invested in their communities.

Thanks for being part of what makes IBO special-and for continuing to show up, share, and support one another as we move this industry forward together.

Disclaimer:  This article was written with the recording transcript using AI.