Dear Friend,
In nearly 30 years of doing this work, I've learned that the most expensive losses don't start with a fire, a lawsuit, or a storm.
They start with four words:
"I thought I was covered."
Not "I knew I wasn't covered." Not "I chose not to buy insurance."
"I thought I was covered."
That's what makes it so dangerous. Because the business owners who say those words aren't careless people. They're responsible. They bought insurance. They paid their premiums on time. They renewed every year. They trusted their advisors.
They did everything right — except question the one thing that mattered most.
Their assumptions.
I sat with a contractor last year who had been in business for over a decade. Solid reputation. Good revenue. Insurance in place since day one. He assumed his commercial auto policy covered every driver operating a company vehicle. Why wouldn't he? He was paying for commercial auto. His trucks were listed. It seemed obvious.
Then one of his crew members got into an accident in a company truck. Significant damage. Injury claim from the other driver. He filed the claim fully expecting his policy to handle it.
It didn't.
The driver wasn't listed on the policy. The policy required scheduled drivers, and this employee had been hired eight months earlier without ever being added. Nobody caught it — not the business owner, not his office manager, not his previous agent.
One assumption. One unlisted driver. And suddenly this man was staring at a six-figure exposure that his insurance wouldn't touch.
He looked at me and said those four words. And I could see in his eyes that he wasn't just worried about the money. He was questioning everything he thought he knew about his own business.
This is what I mean when I say having insurance and being protected are not the same thing.
The problem is almost never a lack of insurance. It's a lack of awareness. Assumptions about what a policy covers. Assumptions about endorsements and exclusions. Assumptions about how claims actually work when the pressure is on.
And here's what keeps me up at night — the strongest leaders I know, the ones who challenge every assumption in their operations, their finances, their hiring, their strategy — those same leaders often never challenge their insurance assumptions. They verify everything else. But their protection strategy? They just trust that it's working.
I'm asking you right now: when was the last time someone challenged YOUR assumptions?
Not your premiums. Not your limits. Your assumptions.
Because that's where the largest risks hide. And by the time you discover them, you're already on the phone with an adjuster who's telling you something you never expected to hear.
That's exactly why I wrote The Prestizia Protection Playbook — to help business owners identify the assumptions that are hiding in plain sight before they become six-figure mistakes.
👉 Get your copy here: https://www.amazon.com/dp/B0GM94983Q
And if you're the kind of leader who refuses to assume — who wants real claim breakdowns, coverage gap analysis, and the protection strategies I've built over 30 years — then Protection Circle Insider is where that work happens every single month.
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Stop assuming. Start verifying. That's what separates the businesses that survive from the ones that wish they'd asked one more question.
Stay protected. Stay passionate. And never let what you've built be taken from you.
John Crist Founder, Prestizia Insurance Author, The Prestizia Protection Playbook