Last week, I had a conversation with a CEO who just crossed a billion dollars in revenue. Yes, billion with a “B.” Big milestone. Big operations. Big targets.
So why was he on the phone with me?
Because his security provider recommended a penetration test. You read that right: the same company responsible for keeping them secure was suggesting someone test whether their security actually worked.
Let that sink in.
This is the equivalent of a chef handing you a steak and then asking if you’d like to send it back to the kitchen for inspection. It raises a bigger, darker question: if they’re so confident in the security they built, why are they asking someone else to evaluate it?
Here’s what we found out: they had done a penetration test. Last year. Same vendor. And the results?
“All clear. Everything looks great. Nothing to see here.”
Of course it did. When you’re grading your own paper, the only surprise is if you don’t give yourself an A+.
Let me tell you a story.
The Farm, The Gate, and The Illusion of Security
I was at my family farm this weekend, and there’s a gate at the end of the driveway leading to the back 40 acres. Padlocked. Solid steel. Unmissable.
Right next to it? A dirt path worn into the grass by truck after truck driving around the gate. So many vehicles had ignored the gate entirely that the ground had given up trying to fight back.
That gate? It wasn’t protecting anything. It was a checkbox. Someone said, “We need a gate,” and they put one in the middle of the road, never thinking that a gate without fences is just decorative security.
And that’s exactly what most cybersecurity looks like when it’s self-evaluated.
We’ve seen it time and time again: the security provider installs controls, then checks their own work using a checklist they wrote. “Firewall in place? Yep.” “MFA enabled? Yep.” “Locked gate across the road? Yep.”
Do they ever look at the tire tracks leading around the gate? Doubtful.
This Is Why CEOs Get Nervous (And Why They Should)
When that billion-dollar CEO called, he wasn’t just curious—he was skeptical. He didn’t trust the self-praise. He was looking for someone who doesn’t build the gate… but inspects whether anyone’s driven around it.
And he was right to worry.
Because if your security vendor is testing their own work, they’re not evaluating threats. They’re evaluating their own checklist.
This is why businesses get ransomed after getting clean penetration test results. Because those tests aren’t designed to uncover reality. They’re designed to validate comfort.
Here’s the Brutal Truth
If you’re not testing your security independently, you don’t know if it works. And if you don’t know if it works, you’re not secure—you’re just lucky. Until you’re not.
And when the lawsuit hits—because it will—they won’t ask who your provider was. They’ll ask why you didn’t validate your defenses.
You don’t get to say, “But the gate was locked.”
They’ll ask, “Why was there no fence?”
Want to Find the Paths Around Your Gates?
We specialize in one thing: finding the weak points the builders missed. We don’t sell firewalls. We don’t manage your help desk. We break things for a living. We identify where the real risks are—before someone else does it the hard way.
If you’re ready for an unfiltered look at your defenses, here’s your next step:
We’ll show you where your gates are wide open and the paths the attackers will take to walk right through.
Because in cybersecurity, looking secure and being secure are two very different things.
And only one of them keeps you out of court.
