3 weeks a month, I’ve been getting a multi-hour infusion of clear, viscous, bubbly fluid… like Crystal Pepsi for my veins. It’s a treatment for my autoimmune disorder and, sidebar, I’m a vampire now. That shit’s a human blood product. And (surprise surprise) nobody offers this weird vampire treatment out in my unincoporated township.

So we’ve been into Philly a lot. (Here comes the actual point!) 

I’ve had a LOT of time to stare out the window at The Big City like an overawed country mouse.

I’ve read so many billboards. SO. MANY. REALLY terrible, no good, very bad, incompetent billboards. 

Billboards, right? Bet you didn’t see that coming. They’re sooooooo meatspace. And yet, billboards are perfectly relevant to we who sell bits and bytes. 

Billboards have a simple yet difficult job: Grab attention, create interest, and be memorable, in very few words. (Just like your headlines!) And most of them fail in every way possible. (Just like your headlines!)

A billboard has to motivate someone who is literally driving away from the message.

And your headline has to motivate someone who is literally more likely to hit the Back button than read your next sentence.

Yep, we’ve all got a lot in common with billboards.

So for our mutual edification, on my last trip I took notes! I wrote down the text and imagery of four billboards we passed while riding into center city. 


  • It’s not just our name
  • It’s our mission 
  • Picture: None, just the name of the business below (“Beneficial”)


  • Lower tuition
  • Top 10 wages 
  • Picture: smiling adult outside office building facing towards The Future™


  • THIS is back surgery
  • We can prevent this 
  • Picture: x-ray of a spine full of bolts and rods


  • Team (TOYOTA LOGO) 
  • We repair all makes and models 
  • Picture: small photo of dealership

Spoiler: Two of these are terrible, one is okay, and one is great. 

Do you know which one is which? If not, you’re about to learn. (And once you learn… you can’t unsee! In the best way possible.)

If you’ve heard of my PDF formula, you know the core of persuasion: Pain, Dream, Fix. It goes a little something like this…

  • Pain — a real problem the reader has now (because nothing is more interesting to a person than their own problems, especially when understood and validated by someone else)
  • Dream — the reader’s ideal of a universe where that pain no longer exists
  • Fix — a real, credible method by which your product can turn their current pain into their longed-for dream

Here’s a video I did about PDF in copy and video about it.

This is a framework for persuasion that has worked since ancient times because it’s not about tricks or “power words” but appealing to the way human nature works. Naturally, people are self-interested. Naturally, they want to better their lives. Naturally, people love when you pay attention to them and really listen. Naturally, that makes them want to agree with you.

So…… right away, if you know PDF, you can spot that only ONE of the billboards uses pain to grab attention. And in this case, it’s literal pain: a gnarly x-ray of a spine full of bolts and rods. Owwwwww. This is madness! NO, THIS IS BACK SURGERY! Dream: WE CAN PREVENT IT. The offering? Sports medicine and physical therapy. Bam!

WINNER: A complete PDF makes Billboard #3 a winner.

Semi-honorable mention: #2 Pain is the most powerful trait to sell with. Benefits come second. Features are the least powerful trait to sell with. So our runner up is all about benefits… lower tuition, higher wages. Okay, but not great. The school logo also says what the program is for (science department?) but in much smaller text and I couldn’t catch the details. So, the benefit speak is pray-n-spray at that. 

First loser: #4 This car repair billboard emphasized TEAM TOYOTA with a giant Toyota logo, then tried to claim “We service all models.” Contradiction ruins a marketing message. And the only way to get the name of the dealer, in case you are somehow economically aroused by bad copy, you had to scan the small and tilted photo of the dealership to get the name. Total fail. But not as total as the bottom billboard, because…

Absolute bottom: #1 At least with the #FAIL car repair billboard, you know it’s about cars, about repairing cars, by a dealer. What the hell is billboard #1 about? WHO KNOWS? Not me. 

“It’s not just our name” — No, no, no, bad copywriters! Nobody cares what your name is. The viewer cares about themselves. Do not talk about yourself unless it’s about how much you will help the viewer. And again, I caught the name of the company — Beneficial — but I have literally no idea what they were trying to sell. Probably because they didn’t try to sell. Or even communicate. FAIL. 

Suffice to say, the reader knowing WTF you’re even trying to sell is a prerequisite for actually making a sale.

I know it’s all pretty hilarious but don’t laugh too hard until you go and assess your own product and blog post headlines. 

Cuz… we’re all guilty of all these problems. Headline writing. Email subject lines. Ads. Yeah. I’m no innocent. I’ve pumped out my share of limp, soggy nightmare billboards. 

Moral of the story: Always picture your prospect driving on by. Then fix your s*!~! 

Here's another thing I wrote about how I boosted conversions 2.4x by applying PDF to my own lazy copywriting btw. Read it… you’ll find it useful!

When in doubt, defer to the wisdom of Burma-Shave:

red warning signs attached to roadside wooden posts


Metaphorically speakin’.

There's more where that came from

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