7 Insurance Mistakes That Can Sink a Contracting Business

Mistakes You Don’t See Until It’s Too Late

Every contractor account I review shows the same avoidable traps — hidden costs, ignored gaps, bad habits that quietly eat profits.

Mistake #1: No Comprehensive Plan
Business and personal coverages aren’t connected. One personal lawsuit can reach your business assets.

Mistake #2: Over-insuring Small Stuff, Under-insuring Big Risks
Too much coverage on tools, too little on lawsuits or major injuries.

Mistake #3: No Long-Term Strategy
Quote-hopping or staying forever with rate-creepers — both cost you.

Mistake #4: “It Won’t Happen to Me” Mentality
One incident (injury, sub mistake, lawsuit) and it’s game over.

Mistake #5: Poor Books = Hidden Premiums
Sloppy payroll classes. No sub COIs. Late audits. Big bills.

Mistake #6: Price Over Value
Same price doesn’t mean same quality. Some carriers make certs and audits a nightmare.

Mistake #7: Not Knowing Enough to Catch a Bad Agent
You don’t need to be an expert — but you do need to be informed.

Quick Win: Spot Your Gaps

  • Are business + personal coverages coordinated?

  • Are your limits where they should be?

  • Are your books clean and audit-proof?

  • Are you thinking long-term — or just about this year’s premium?

Why I Care?
Bad policies don’t hurt when nothing goes wrong. But when they do, they explode. My job is to make sure that doesn’t happen.

Bottom Line Clean it up now — or pay the price later.

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The One Move Every Established Contractor Should Make

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7 Secrets to Lower Premiums Without Risking Coverage