I started building billboards straight out of college, with no knowledge of what I was doing and not much capital to work with. All I had was the desire to make money and an almost equally powerful fear of failure. Starting from scratch, it took me almost a year to find my first location. And even then, nothing came easy since I had absolutely no idea how to rent the ad space or build the thing. But I “endeavored to persevere”, as Teddy Roosevelt would say, and I was able to stick with a pace of building two billboard faces per month for about 15 straight years. At that point, I had 300 billboard faces, which made me the largest privately owned billboard company in Dallas/Ft. Worth. And I did that despite the fierce competition – there were no less than 60 billboard companies operating in Dallas at that time. Every ground lease and every advertising lease was virtually hand-to-hand combat to obtain.

When I sold to Universal Outdoor of Chicago in 1996, I was suddenly rewarded for all that work in one giant windfall. Not that life had been all that bad up to then – I had paid myself a decent salary for most of that time, and I actually enjoyed the fierce competition (as long as I was winning). Immediately after selling, I got a thrill out of calling the automated account center for Charles Schwab and listening to my account balance – I’d sometimes call it four or five times a day. I had never really had much in my account before, and suddenly having seven digits in there was very exciting.

So can you do what I did? Absolutely, if you know what you are doing and have as much desire as I had. In fact, you will have a few advantages over me:

• Instead of taking years to learn what you are doing – how to find locations, build locations and rent advertising space – you can learn that up front with a Home- Study Course or Billboard Boot Camp event.

• Through industry consolidation, the number of competitors out there has been reduced by about 80%. In most markets, there are now only three or four billboard companies as adversaries, instead of thirty or forty.

• Billboards have become one of the strongest media options for advertisers, whereas just a decade ago, it was considered the weak sibling to television, radio and newspapers. The advent of the internet destroyed those giants, but left billboards unscathed.

• The amount of traffic and readership passing billboards increases every day, as does the length of time the cars are stuck in front of signs, due to the endless back-ups on most of America’s major highways and roads. This leads to higher advertising rents – which have already been going up an average of 10% per year.

• New billboard locations are being created every day through new road construction and re-zoning of agricultural land. And small towns across our country are growing into thriving markets that are well served by outdoor and will become the next major cities.

• Vinyl technology has made the installation and quality of advertisements far higher than back when we used to have to hand-paint the signs on 1,000 pound panels to install with a crane, or even worse – up on the signs balancing on a two foot wide catwalk battling the elements. And the range of creative options is incredible: you can have the entire sign as a huge photograph. This has created happier advertisers and more products and services that advertisers can market.


Some people pine for the “good old days”. Well, the “good old days” of outdoor advertising are right now. The industry is in the strongest position it has ever been in.

“But what about the recession”, you may say? Well, here’s the truth about that. I was able to double the size of my billboard operation during the 1980’s recession. And those were the best signs in my inventory, by far. Because, during a recession, you can buy out your competitors for a dime on the dollar – often buying the assets from a lender who have foreclosed. And the poor ad market makes many “mom and pop” owners throw in the towel and sell you their inventory for little more than what they paid. And the sudden decrease in competition from all the large companies, that are forced to regroup, gives you a virtual “free pass” to attack at will all the remaining legal locations. If you look at the billboard company I sold as two distinct pieces, the portion that I built before the recession was not in the ballpark as valuable as the portion I built during the recession.

Is the billboard business an easy way to make money? No. Is it a great way to make money? Yes. You can make a million dollars in it if you know what you are doing and are willing to put in the effort.

And there’s one more thing you should know about the billboard business. It is possible to make huge money in billboards without a penny of capital, or ever borrowing from a bank. There is a unique opportunity to “flip” billboard leases and permits. Basically, you obtain a ground lease for a billboard and the necessary permits and then sell that package to a larger billboard company. How much can you make? At the lowest end, about $5,000 per location. But it is more normally about $20,000, and can range up to $100,000+. And the billboard companies are happy to take them off your hands, as they depend on buying leases and permits to grow their own operations. Few larger billboard companies staff employees to hunt for locations – it is cheaper and more efficient to buy them from other people.