Stuff Goes Sideways. Make Sure It’s Not Fatal.
Let’s be clear:
You don’t buy insurance because you expect something bad to happen.
You buy it because when it does happen—and it will—you can keep going.
The game isn’t risk elimination.
It’s risk transfer.
When you don’t have the right coverage, one accident, one lawsuit, one bad day can wipe out everything you’ve built.
Here’s what you actually need—and what happens if you don’t have it.
1. General Liability
What it covers:
- Bodily injury to a non-employee (customer trips, falls, gets hurt on site)
- Property damage to someone else’s stuff (scratch a car, flood a room, break a window)
- Basic legal defense if someone sues you for physical harm
If you skip it:
- A customer trips on your extension cord—breaks a wrist. They sue.
- Your tech leaves a hose running and floods a lobby. The owner sends you the repair bill.
- You drop a ladder on a $70K glass storefront. It’s all on you.
Real talk:
This is non-negotiable. If you walk onto anyone else’s property, step into their house, or touch anything they own—you need general liability. Period.
Most vendors, customers, and municipalities won’t even let you bid without proof of this.
2. Commercial Auto
What it covers:
- Vehicle accidents while driving for work
- Damage to your work trucks
- Injury or property damage to others in a crash
- Legal claims from accidents in company-owned or business-use vehicles
If you skip it:
- Your tech rear-ends a Mercedes in the company van = full personal liability
- You cause a wreck while hauling materials to a jobsite = your personal auto won’t cover it
- You list your work truck under your name = your business has zero protection
Don’t assume:
- Personal auto policies don’t cover business use.
- If it’s branded, loaded with gear, or used for anything paid—you need a commercial policy.
If the vehicle works for the business, it needs to be insured for the business.
3. Workers’ Compensation
What it covers:
- Medical bills and lost wages for injured employees
- Protection from employee injury lawsuits
- Death benefits in worst-case scenarios
Florida Requirement:
- Required for most non-construction businesses with 4+ employees
- Required for construction-related businesses with just 1 employee
If you skip it:
- Your helper falls off a ladder and breaks his back. He sues for lost income. You’re bankrupt.
- A painter inhales fumes, ends up hospitalized. You’re on the hook.
- Someone files a report—DBPR, DOL, or the state steps in. You get fined and shut down.
Also:
1099 ≠ immunity. If the worker is uninsured, unlicensed, and under your control—they’re your employee in the eyes of the law.
4. Professional Liability (a.k.a. E&O Insurance)
What it covers:
- Financial harm caused by your advice, oversight, or service error
- Missed deadlines, botched designs, faulty specs, or poor guidance
- Lawsuits over claims like “You cost me money”
Common in:
- Architects
- Engineers
- Consultants
- Bookkeepers
- Home inspectors
- IT pros and software installers
If you skip it:
- You mislabel a blueprint and the install goes wrong—$50K rework
- Your consulting advice tanks a client’s business—hello lawsuit
- You accidentally delete a client’s files—expect a claim
General liability covers physical damage.
E&O covers reputational and financial damage from your decisions.
5. Cyber Insurance
What it covers:
- Data breaches
- Ransomware attacks
- Client information leaks
- Business interruption from cybercrime
If you skip it:
- Your CRM gets hacked—customer credit cards exposed. You’re liable.
- Ransomware locks your job tracking system—shuts down operations for a week
- Your assistant clicks a phishing email—$10K of invoice fraud gone before lunch
Who needs it:
If you collect customer info, run software platforms, or store payment data—this is your modern fire insurance.
6. Umbrella Insurance
What it covers:
- Adds extra coverage on top of your other policies
- Kicks in when a claim exceeds your GL, Auto, or Workers’ Comp limits
- Helps with big lawsuits or catastrophic losses
If you skip it:
- A customer sues you for $1.5M. Your GL caps at $1M. You cover the rest.
- An accident injures multiple people. Your auto policy taps out. Umbrella covers the spillover—or doesn’t, if you don’t have it.
What about stacked insurance?
Stacked insurance typically refers to auto liability coverage, where multiple policies (or multiple vehicles under one policy) are “stacked” to increase total coverage in a claim. This is more common in personal auto, but in commercial settings, stacking often happens by layering umbrella or excess liability on top of your General Liability, Commercial Auto, and Workers’ Comp policies.
If your base GL or Auto policy caps at $1 million, and your umbrella adds another $2 million, your total coverage becomes $3 million—that’s stacked protection.
Stacked = layered = protection beyond the first limit.
Why it matters:
Lawsuits are getting bigger. So are judgments. If you’re building anything worth protecting—umbrella insurance keeps the whole house from burning down.
7. Business Owner’s Policy (BOP)
The starter bundle for small business coverage
What it is:
A BOP combines several core policies into one simplified package, usually at a discount. It’s a go-to for small businesses who need coverage without the complexity of building it a la carte.
Typically includes:
- General Liability
- Business Property Insurance (tools, inventory, equipment)
- Business Interruption (loss of income due to fire, flood, or forced closure)
- Sometimes Cyber, E&O, or Employment Practices Liability depending on the carrier
Why it matters:
- One policy, one premium, one renewal date
- Simplifies the insurance stack for solo and small operators
- Often cheaper than buying individual policies
If you skip it:
- You might miss key coverage areas (property damage, stolen tools, equipment loss)
- You’ll likely overpay by stacking policies manually
- When disaster hits—fire, theft, hurricane—you’ll find gaps you didn’t know were there
If you’re a tradesperson, solo operator, or just getting your business off the ground, ask your broker if a BOP makes sense. It’s often the cleanest way to check the big boxes while you’re small.
8. Errors & Omissions (E&O)
A.K.A. Professional Liability—worth its own section.
What it covers:
- Mistakes, negligence, bad advice, or missed details that cause a financial loss to your client
- Claims like:
- “You gave us bad instructions”
- “Your report cost us money”
- “You didn’t deliver what you promised”
Who needs it:
- Anyone advising, inspecting, recommending, or certifying
- Common in:
- Home inspectors
- Real estate professionals
- Consultants and coaches
- Bookkeepers and payroll services
- Designers, architects, engineers
- Any contractor offering inspections, estimates, or warranty-backed advice
If you skip it:
- You leave yourself exposed to lawsuits for non-physical damage
- A simple missed detail in a report or spec sheet could cost thousands
- Your GL policy won’t cover “bad advice”—only physical injury or property damage
E&O protects your judgment. If your business involves plans, evaluations, or expertise—it’s a must.
9. If You Use Subcontractors, 1099s, or Day Labor
Their coverage isn’t your coverage.
The misconception:
“They’re not my employees, so I’m not responsible.”
Wrong.
If they work under your direction, wear your shirts, drive your truck, or follow your schedule—you’re on the hook if something goes sideways.
Here’s What to Watch:
Auto Coverage
If your 1099 or subcontractor is driving their own vehicle for your business, and:
- They get into an accident
- They’re uninsured or underinsured
- The job was yours, and they were fulfilling it for your customer
Guess who’s next in line to be sued? You.
Always require subcontractors to carry Commercial Auto insurance if they’re driving for work.
Liability & Workers’ Comp
If your subcontractor or 1099:
- Damages a customer’s property
- Gets injured on the job
- Hurts someone else during work hours
And they don’t have:
- General Liability
- Workers’ Comp
- Umbrella coverage (optional but smart)
That exposure passes straight to you.
In Florida construction trades, workers’ comp is mandatory for subcontractors. If they don’t have it, the state treats them like your employee.
What to Do About It:
- Collect COIs (Certificates of Insurance)
- Don’t take their word for it
- Check expiration dates
- Make sure your business is listed as the certificate holder
- Get it in writing
- Subcontractor agreement = non-negotiable
- Require proof of coverage before they touch a job
- No insurance, no job.
It’s not personal—it’s protection.
10. Final Word
You can’t control everything.
But you can control whether a bad day becomes a bad year—or the end of the road.
Insurance doesn’t prevent chaos. It buys you the right to recover.
So don’t just pick the cheapest quote.
Don’t let your cousin “who used to sell insurance” slap together a policy.
And don’t assume you’re covered because you “have something on file.”
Ask your broker hard questions.
Know what’s excluded.
And make sure the protection matches the risk.
Because it’s not a question of if something goes wrong.
It’s when.
And when it does—make sure the bill doesn’t land in your lap.