ToolHut Trade School · Toolkit
Where to start looking for insurance
"Talk to an agent" is honest advice and nearly useless if you have never bought a policy and do not know an agent. So here is the shape of the market, what each kind of place is actually good for, and what to ask.
First, what you are buying
General liability (GL) covers damage your work does to other people and their property. Workers' compensation covers people who work for you — and the rules for a solo owner vary by state. Commercial auto matters because a personal truck policy can deny a claim that happened during work use. A certificate of insurance (COI) is the one-page proof, and it is what a general contractor will ask for before you set foot on site.
Where contractors commonly start
Places you with several carriers
An independent agent who writes trades in your state
An independent agent quotes you across several carriers rather than one, knows what trades your size actually carry locally, and is the person who answers the phone when a general contractor needs a certificate on a Friday afternoon. Calling two or three costs nothing but the time.
Ask them: What limits do trades my size carry around here, what does this policy exclude that bites people in my trade, and what does it cost in money and hours to issue a COI?
Fast quotes, GL and workers' comp
Online small-business insurers
Several insurers now quote and bind small-business policies entirely online, which suits a solo operator who needs a certificate quickly. ERGO NEXT is one — it was Next Insurance until Munich Re's ERGO completed its acquisition in July 2025 and the company rebranded in January 2026, so you may still see both names. biBerk is Berkshire Hathaway's direct small-business arm, and Berkshire Hathaway GUARD is a separate Berkshire carrier that writes workers' comp through agents.
Ask them: Is the quote bindable today, what is the audit process at the end of the year, and can I get a certificate issued same-day when a GC asks?
Commercial auto first
Carriers that bundle with your truck
If the truck is already the expensive policy, bundling can be worth pricing. Progressive is the obvious one, with a multi-product discount on commercial auto when you hold an in-force business owner's policy or general liability. Worth knowing how it actually works: Progressive underwrites the commercial auto itself, and for general liability and workers' comp it acts as an intermediary placing you with other carriers — so the liability policy is somebody else's paper.
Ask them: Which part of this is underwritten by you and which is placed elsewhere, and who do I call when there is a claim on each?
Workers' comp when nobody else will write it
Your state fund or assigned-risk pool
Most states have a fund or a pool that writes workers' compensation for businesses the open market declines — new, small, or in a trade a carrier does not like. It is rarely the cheapest option and it is not nothing: it is the reason a brand-new roofing business can get covered at all. Your state's department of insurance or workers' compensation board will say what exists where you are.
Ask them: Am I eligible for the voluntary market first, and what would it take to get out of the pool next year?
Two things that catch people
The year-end audit. Workers' comp is priced on estimated payroll and reconciled afterwards. If the real payroll was bigger than the estimate, the difference is owed, and that bill lands long after the money has been spent. Ask what triggers an audit and what the carrier counts as payroll before you sign.
The policy that excludes you. A minimum-premium workers' comp policy that leaves the owner off it is often called a ghost policy. It buys the certificate. It does not cover the owner at all. It is a reasonable purchase for a true solo operator who needs the certificate to work. It stops being reasonable the moment anyone else works for you and is not added. The lesson in Legal Day One covers the whole of it.
Legal Day One
Insurance before the first job, the order of operations, the license question, and the policy that exists only for the certificate. Free with any ToolHut account.
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