Dear Friend,
I want to share my favorite question — the one that changes the entire conversation every time I ask it.
It's not about premiums. It's not about carriers. It's not about limits or deductibles.
It's this:
"What's changed in your business over the last 12 months?"
Most business owners pause when I ask that. Not because they don't know the answer. Because nobody has ever asked them before. Their current agent talks about renewal dates and rate increases. Nobody sits down and asks what's actually happening inside the business.
And yet — think about how much changes in a single year. Revenue shifts. Payroll grows. You hire new people, add vehicles, sign bigger contracts, take on subcontractors, open a new location, upgrade your equipment. The business you're running in June is not the same business you were running last January.
Now here's the question that should keep you up tonight:
Did your protection strategy change with it?
Because growth isn't just opportunity. Growth is exposure. Every new employee, every new contract, every new truck on the road creates risk that didn't exist before. And if your insurance program is still structured for the business, you were running two or three years ago, you're carrying gaps you can't see.
I sat with a business owner recently who had doubled her revenue in 18 months. She was proud of it — and she should have been. But when I asked her that one question, her face changed. She realized that in all the excitement of growing, nobody had connected the dots between her success and her exposure. Her policy hadn't been restructured since she was doing half the volume with half the team.
She wasn't negligent. She wasn't careless. She was busy building something incredible. And the system around her — her agent, her renewal process, her annual review — never once asked the question that mattered.
That's the difference between an insurance review and a protection review.
Most reviews focus on cost — what does this policy run, can we shave the premium, when does it renew. Those things matter. But they don't tell you whether your protection structure still fits the business you're actually operating today. And that's the conversation that prevents the kind of losses I've spent 30 years watching business owners suffer through.
The strongest leaders I work with don't wait for renewal season to think about protection. They treat it the way they treat everything else in their business — with intention, with strategy, and with the understanding that what got them here won't protect them where they're going.
That's not just smart business. That's stewardship of everything you've built.
So let me ask you directly: when was the last time someone sat down with you and asked what's changed? Not your premium. Not your rate. What's changed in YOUR business — and does your protection still match it?
If the answer is "I'm not sure," that's not a failure. That's a starting point. And it's exactly why I created Protection Circle Insider.
Every month inside the circle, I walk members through the same strategic review process I use with my own clients — real claim breakdowns, coverage gap analysis, and the hard questions that prevent expensive surprises. This isn't surface-level insurance talk. It's the work that separates business owners who are covered from business owners who are truly protected.
👉 Join Protection Circle Insider — $29/month: https://www.theprotectioncircle.com/upgrade
And if you want to start rethinking your protection strategy right now, The Prestizia Protection Playbook was written for this exact moment — when you realize there might be something you're not seeing.
👉 Get your copy here: https://www.amazon.com/dp/B0GM94983Q
Don't wait for a claim to answer the question nobody's been asking.
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