What if an old roadside billboard could generate $30,000 to $40,000 a year, then be converted into an asset producing $150,000+?
In this episode of JackQuisitions, Jack Carr breaks down the billboard business, including how billboard owners make money, what makes certain locations so valuable, and why converting a static billboard to digital can dramatically increase its revenue potential.
Jack covers billboard pricing, permits, ground leases, traffic counts, digital conversions, and how he would approach buying his first billboard in a market dominated by major operators like Lamar Advertising.
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In this episode, Jack covers:
• How billboard businesses actually make money
• Why permits and location can be more valuable than the billboard itself
• How a static billboard can generate $30K–$70K+ per year
• Why digital billboards can produce $150K+ from the same location
• The ground lease mistake that can destroy a billboard investment
• What Jack would look for when buying his first billboard
• Why smaller markets and overlooked locations could offer the best opportunities
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Imagine you're driving and you pass that old rusty billboard. There's a chance that that ugly steel pole is producing $30,000 to $40,000 a year in revenue. And if it happens to be in the right location with the right permits, there may be a way to turn that same billboard into something that produces $150 to $180K a year. No new location, no new piece of land, same pole. And by the end of this video, I'm gonna tell you exactly what I would look for if I wanted to buy one of these things because the most valuable part of a billboard isn't actually the billboard. So let's say I find a billboard for sale. It's a static two-faced billboard besides a busy highway, maybe here in Nashville, maybe LA, wherever, maybe it's producing probably around $3,000 a month per face, $72k a year. You find a business that wants the exposure, you sell them the space, you print a giant piece of vinyl and put it on the board, collect rent, and repeat. But that's not what I really think I'm
buying. More specifically, I'm buying the right to monetize that location because you can't just buy a piece of land beside the interstate and throw up a 50-foot billboard whenever you feel like it, right? There's federal, there's state, there's DOT, there's local restrictions on outdoor advertising, plus zoning, spacing, permitting setbacks, and in some markets, outright bans on new billboards, which means that the old billboard, the old permitted billboard locations can be extremely valuable because you're not allowed to build another one. And that changes the way I look at these deals. So who owns the land underneath? Does a billboard company own the dirt? Usually not. If the rent's fixed, or is the landlord taking 20% of the revenue? Can I convert the sign to digital, which is huge for later? What's the traffic count on that road or highway? Can drivers actually see the thing? Is it right hand side? Is it left-hand side? Are there trees growing in front of it? And most importantly, what is making today versus what it should be making? Because this is where the story gets interesting,
right? Is Lamar Advertising is one of the biggest billboard companies in America. And as publicly talked about static interstate billboards doing $3,000 a month. I've bought billboards for my business before, like it's it's about $3,000 per month. They spend over $200,000 converting a static billboard to digital. Why? Because that same location can do roughly $15,000 a month. So that $36k a year for that double side is now becoming $180K. And that's because a static billboard just has that one advertiser, whereas digital rotates through six, seven, eight advertisers on the same screen. Now I'm selling inventory multiple times for that same location, and it's not some tiny experimental part of the industry. This is a thing, this is a huge thing. Because by the end of 2025, Lamar had 159,000 billboard displays, and around 5,500 of them are digital, and they're actively converting as we go.
So this is why the lease matters so much. Because if I buy the billboard with three years left on it and the ground lease expires then, and I spend 200k converting it to digital, I may just have improved someone else's property. I want to have a long-term control on the site. Ideally, I even want to own the land. If I can't, I want a long enough lease with extensions and economics so I don't destroy the upside and I can actually benefit from some of that. Lamar's lease expense was around 17% of their revenue in 2024. While some competitors with more expensive locations were paying dramatically more, like that tells you something. It's simple but not easy. It's not just selling ads, it's really a real estate business hiding inside an advertising
company.
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your call today. And now here's where we get to where I promised at the beginning is I wouldn't start by just going out there and trying to buy the biggest billboard, the best producing billboard ever. I'd actually focus on the tier two, tier three billboards that are only doing side streets or smaller markets or smaller car counts because those ones are ripe for conversion and I can get my feet under me and build those muscles to start advertising and start to have people understand my name and know who to call in the industry when they're looking for some advertising spend. The second spot I would start is I would look in places others don't. There's a story in the billboard space of a few years ago where somebody went and instead of buying regular billboards, they went and built billboards on tribal land. So they went in, they had some connection with tribal leaders, they went into the reservations, and because the the laws and the rules are different, they were able to partner with the reservation, build a bunch of these billboards, and collect revenue. They had to think outside the box on how to win because Lamar is such a monopoly in the space, and the billboard companies that are currently in place are such monopolies in this space that you're gonna have to kick and claw your way into this industry. If you like what you heard, if buying billboards has interested you in any way, shape, or form, maybe we'll go out and do one on the show. Who knows? We'll see. Like, comment, subscribe. If I get here, we'll do this. If I get 10,000 likes, which is never gonna happen, I will go buy a billboard. I'll figure it out. I don't care. I'll go buy the worst producing billboard in Nashville. Uh 10,000 though. 10,000 is a lot of likes. So like if you like what you heard, subscribe, share, tell your mom to like this as well so that uh we can go embarrass I can go embarrass myself buying billboards. All right, guys, catch you next time.
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