Dear Friend,
In nearly 30 years of doing this work, I've sat with business owners on the best days of their lives and the worst. I've been in the room when someone signed a contract that doubled their revenue. And I've been in the room when someone found out their insurance wouldn't cover the loss that just changed everything.
Through all of those conversations — hundreds of them — I've noticed something that haunts me.
The regrets are almost always the same.
I've never once heard a business owner say, "I wish I had spent less time preparing." I've never heard, "I wish I had asked fewer questions about my coverage." I've never heard, "I wish I hadn't reviewed my risks so carefully."
But I have heard this — more times than I can count:
"I wish I had known."
I wish I had known the policy didn't cover that. I wish I had known the contract transferred the liability to me. I wish I had known the replacement cost hadn't been updated. I wish I had known cyber wasn't included. I wish I had known before the claim happened.
Every single time, the information was available. The gap was identifiable. The fix was affordable. But nobody looked. Nobody asked. And by the time the business owner found out, the only thing left was regret.
I remember sitting with a restaurant owner after a kitchen fire destroyed most of his equipment. He'd been in business for eleven years. He had a commercial property policy. He assumed it would cover the replacement cost of everything he'd lost.
It covered a fraction.
His policy was still using equipment valuations from when he originally purchased the coverage. In eleven years, he'd upgraded his kitchen twice, added a bar program, installed a commercial ventilation system. None of it had been updated on the policy. The premium stayed low because the coverage stayed frozen in 2013.
He didn't cry in my office. He just sat there, quiet, staring at the numbers. Then he said, "I renewed this policy every single year. How did nobody catch this?"
That's the question that stays with me. Because the answer is simple and terrible: nobody caught it because nobody looked. The renewal was a transaction — sign here, pay this, see you next year. Nobody sat down with him and asked what had changed. Nobody walked through the actual coverage against the actual business. And now the cost of that missing conversation was six figures.
The tragedy is never that something went wrong. Things go wrong in business — that's inevitable. The tragedy is discovering too late that it was preventable.
Every business owner faces two paths. The first is easy: assume everything is fine, assume someone else has checked, assume the coverage works, assume the risks are handled. That path feels comfortable right up until the moment it isn't.
The second path requires leadership. Review. Verify. Understand. Prepare. That path takes time and intention. But it's the path that eliminates future regret. And I've never met a business owner on the other side of a loss who wished they'd taken the easy path.
Preparation may feel expensive until you compare it with the cost of regret. And regret is always more expensive.
So, let me ask you a question worth sitting with: if a major loss happened tomorrow, what would you wish you had reviewed today? Don't rush that answer. Write it down. Whatever you just thought of — that's where your risk lives. And that's where your next conversation with your broker should start.
If you want to make sure that conversation happens before life forces it, that's exactly what Protection Circle Insider is built for. Every month, I walk members through real claims where avoidable regret became unavoidable reality — the specific gaps, the specific language, the specific decisions that made the difference. So you can learn from other people's mistakes instead of paying for your own.
👉 Join Protection Circle Insider — founding rate, $29/month: https://www.theprotectioncircle.com/upgrade
And if you want to start identifying what you don't know about your own coverage, The Prestizia Protection Playbook was written for exactly that — the moment you decide that "I wish I had known" is something you'll never have to say.
👉 Get your copy: https://www.amazon.com/dp/B0GM94983Q
The goal isn't to eliminate every risk. That's impossible. The goal is to eliminate avoidable regret. And that starts with one decision — the decision to look before life makes you.
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