I just got back from a business event.

Big room. Lots of suits. Over 400 CEOs and CFOs packed into one space, armed with business cards, ambition, and an alarming amount of espresso.

I went in thinking, This is it. This is where we talk about cyber liability. This is where the lightbulbs go off.

Yeah, no.

Huge lesson learned: They. Don’t. Care.

You say “cyber liability,” and their eyes glaze over faster than a donut at a police convention.

No panic. No urgency.

Just polite nods and a mental note to never sit next to me at lunch again. I was trying to figure out why. Here’s the answer: if you don’t have a relationship, they hear “cyber liability” and think “not my problem.” It’s not personal.

It’s just that when you’re worried about sales goals, capital raises, and whether your COGS line is going to tank your Q3 bonus, cyber liability sounds about as urgent as updating the office recycling plan.

How I Accidentally Fixed the Problem

After about 20 painfully awkward conversations (yes, I took notes because that’s what nerds like me do), I tried something different.

Instead of leading with “We help you manage your cyber liability,” I said this:

“We perform penetration testing. How do you know your current IT provider is actually protecting you?”

Of course, I had to explain what that meant — because most CEOs think “pen test” sounds like something you get at Office Depot.

So I put it simply:

“A penetration test is when you pay us first to break into your network — on purpose. We find the cracks, show you how we got in, and help you fix it before someone nasty finds them.

With hackers? You pay them after they break in — and it’s a lot more expensive, a lot less fun, and sometimes ends with a courtroom and a headline you never wanted.”

That usually got a laugh.

More importantly, it snapped people awake.

Because now they understood: Pen testing isn’t an optional extra. It’s preemptive disaster control.

Interest.

Real questions.

Actual conversations.

Suddenly, people were leaning forward. Asking questions. Wanting to know more.

Acceptance rate for moving to the next step (an actual assessment)?

North of 50%.

Meanwhile, whenever I opened with cyber liability talk? Dead on arrival. They didn’t feel like they had a risk.

No risk = no urgency = no deal.

Penetration Testing: The Gateway Drug

Here’s the magic:

When you talk about penetration testing, you’re talking about them — their provider, their exposure, their personal oh-crap risk. It’s immediate. It’s tangible. It hits them where it hurts.

Then, once you get their attention with that, you can layer in the cyber liability conversation.

Not the other way around.

Never the other way around.

If you start with “cyber liability,” you’re selling life insurance to someone who thinks they’re immortal.

If you start with, “Hey, your current provider might be asleep at the wheel,” you’re selling seatbelts to a guy who just watched a car crash.

Big difference.

Here’s the Plan

I’m going to be digging deeper into this — with the data, scripts, and actual field-tested conversations — during the first day of Galactic Universe.

Because let’s be honest:

You’re not just an MSP owner anymore.

You’re in the risk transfer business.

You’re in the prove-your-worth-before-you-get-sued business.

And you can’t afford to keep guessing what makes CEOs and CFOs actually move.

(Trust me: it’s not a glossy flyer about compliance frameworks.)

If you want to shortcut the pain and start getting real traction with decision-makers, you’ll want to be in the room.

I’ll show you exactly what worked, what didn’t, and how to frame penetration testing and cyber liability together to create that Oh wow, tell me more moment.

See you at Universe.

Bring questions. Bring caffeine.