Domain Digital

Why Smart Leaders Still Get Breached

Yesterday I told you about the 8:35PM PM call.
The one where a business owner begged me to undo a ransomware attack that had already destroyed their operation.
I got a few messages on this.
Some said, "How could they let this happen?"
Here's the part that keeps me up:
They didn't let it happen.
They just tested too late.

Let me tell you what that managing director told me during our second conversation (yes, we spoke again).
They had a bit of cybersec.

Antivirus on every machine ✓
Firewall at the perimeter ✓
Password policy enforced ✓
MFA ✓
Annual security "training" (a 20-minute video) ✓
Cyber insurance policy ✓
On paper? They looked compliant(ish).
In practice?

→ No one was monitoring logs in real time
→ No one knew an attacker had been inside their network for 19 days before encryption started
→ No automated response to isolate infected endpoints
→ No tested backup restoration process (they had backups — but no one had ever tried to actually restore from them under pressure)

They had stuff in place. They just never tested if it actually worked.

Here's the uncomfortable truth I've learned after 20 + years in this industry:
Most executives don't fail because they're cheap or careless.
They fail because they treat cybersecurity like insurance instead of infrastructure.
You buy it. You file it. You assume it's working.
And then one day, you find out it wasn't.

If your business has 20-150 seats, you're in the super danger zone.
Not because you're a juicy target. But because you're big enough to have complexity and small enough to lack dedicated security staff.
That's the gap attackers love to explore.
The gap between "we have something in place" and "we've actually tested it under fire."

So here's my question for you:
When was the last time you tested your security?
Not "reviewed the policy."
Not "renewed the subscription."
Tested.
Can you detect an intruder in your environment right now?
Can you isolate a compromised device in under 60 seconds?
Can you restore your most critical system from backup in under an hour?
Do you even know what logs you're collecting — or if anyone's watching them?

If the answer is "I don't know" or "probably not," you got yourself an issue.
You're just waiting for the call.

Tomorrow: I'll share what actually works and why it's simpler than you think.
Comment or DM me if you want to talk about where your gaps might be. I'll tell you the truth, even if it's uncomfortable. I am well known for being a straight shooter.

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The surge in AI-related activities is causing a strain on the availability of components, which in turn is driving up prices for computing devices.

If you’re considering buying any tech gear, it’s smart to act now.

Prices are rising and might I say, disturbingly fast. A heads up is always better than a surprise….

(The irony that AI created this image did not fly under the radar)