Most businesses don’t fail because of competition. They fail because of a preventable mistake that comes back to bite them at the worst time. In almost every insurance review I’ve done over the last 25 years, I find landmines waiting to go off: gaps, poor bookkeeping, or coverage that was never explained
My goal is to handle the “insurance shit” so you don’t have to.
Here are the 7 most common mistakes I see—and how to fix them before they cost you
Mistake #1: Having No Coherent Plan
Most owners collect policies like puzzle pieces that never fit. One policy here, another there, with no one looking at the big picture.
- The result: You have overlaps in some areas and gaping holes in others.
- The fix: Work with one advisor who organizes both business and personal coverage under a single, clear strategy.
Mistake #2: Insuring the Small Stuff
Too many owners waste money on low deductibles or gimmicky add-ons while leaving their biggest risks exposed.
- The fix: Put your dollars where they matter most—liability, workers’ comp, vehicles, and property. Use insurance for disasters, not annoyances.
Mistake #3: Playing the Short Game
Jumping from carrier to carrier every year might feel like “smart shopping,” but it destroys your long-term pricing power.
- The fix: Stay the course for 3–4 years to qualify for loyalty credits and top-tier programs. Shop strategically, not frantically.
Mistake #4: Ignoring the Audit
For contractors and restaurant owners, your audit isn’t just paperwork—it determines your premiums.
- The fix: Keep clean books and accurate payroll. Sloppy records lead to higher premiums every single time.
Mistake #5: Not Protecting Against the “Big One”
- A $2,000 loss won’t sink you, but a six-figure lawsuit or a total property loss will.
The fix: Ensure your limits are high enough to protect your life’s work. If I were in your shoes, this is the first thing I’d check.
Mistake #6: Letting Renewals Run on Autopilot
Too many owners sign renewals without a second thought. Meanwhile, carriers may quietly adjust terms or strip away coverages.
- The fix: Treat every renewal as a strategic review. It’s a chance to find ways to cut back premiums and fix gaps
Mistake #7: Choosing Price Over Partnership
The “cheapest” quote is often the weakest. You only realize how expensive a cheap policy is when you file a claim and find out you aren’t covered.
The Bottom Line
This won’t be a waste of your time. Even if you don’t end up switching, a review will give you a clear list of ideas on how to save money and where your current gaps are.