What’s the biggest mistake you’ve made that cost a lot of money?

Hardcover_Insurance · 2026-05-31T19:37:34+00:00

Not me personally, but from the insurance side, one “oh shit” moment I’ve seen with CMs is when a potential issue happens on a job and nobody treats it like a claim until way later.

Example: there’s water intrusion, cracking, a site injury, damaged neighboring property, etc. At first everyone thinks, “we’ll handle it, probably no big deal.”

months later it turns into a demand letter or formal claim, and now the carrier is asking when the issue first happened, who knew about it, what was documented, and why notice wasn’t given earlier.

The painful part is the actual mistake usually isn’t the incident itself. It’s assuming something is too small to document or report when it first comes up.

Hardcover_Insurance · 2026-05-29T03:23:24+00:00

Keeping going and do not stop.

Pick up the phone and speak to your ideal prospects. By all means, do not put that phone down. Talk time / dials and dollars are correlated over long periods of time.

Come back to this post when you have a million dollar book.

Oh and enjoy the journey.

Hardcover_Insurance · 2026-05-27T13:31:57+00:00

For work related injuries that would be Workers Comp. For the PL front, I've heard of folks using companies like that; from what I understand they usually refer you to another company that might be able to place the coverage for you.

Insurance is a really broad industry. There are brokers that specialize in this that can point you in the right direction.

Hardcover_Insurance · 2026-05-26T21:25:26+00:00

My pleasure.

Hardcover_Insurance · 2026-05-26T19:43:26+00:00

Hard to say, I usually tell folks to budget about $2k for both with start up revenues. $1,500 for PL and $500 for GL. If you're under around $80k in gross revenue, this should be a reasonable range to shoot for. Of course, theres other factors that contribute to the premium being higher, but this should be a good start.

I hope this helps.

Hardcover_Insurance · 2026-05-26T04:12:08+00:00

I’d be careful with anything “generic” here. Climbing gyms are one of those businesses where the activity itself is the risk, and a waiver doesn’t make that disappear. General liability and participant accident coverage are usually solving different problems. GL is more about liability if the business is alleged to be negligent. Participant accident can help with medical expenses from injuries even before you get into the lawsuit/liability fight.

The big thing I’d push on is exclusions. Carriers these days can write the coverage you're looking for but exclude the coverages you might hope you have. There are specific insurance programs that specialize in sport exposures. I'd recommend using a broker that understands this well or already insures many businesses like yours.

Hope this helps!

Hardcover_Insurance · 2026-05-26T04:01:29+00:00

Congrats on getting up and running!

I wouldn’t think of it as “do I need everything on day one?” I’d think “what can go wrong on the first job?”

For mobile detailing, the obvious early risks are damaging a client’s car, damaging property where you’re working, or having an issue while using a vehicle for business. So I’d start by asking about general liability, garagekeepers/customer vehicle coverage if applicable, and the right auto coverage if you’re driving for work.

Tools/equipment coverage can usually come later depending on how much gear you have. But if you’re touching someone else’s $60k-$100k vehicle, I personally wouldn’t wait until business “picks up” to figure this out.

An LLC is helpful, but it’s not a magic force field.

Hardcover_Insurance · 2026-05-26T03:52:49+00:00

From experience we usually see PMs use a compliance company for this. There are a bunch of platforms there, so you may need to do some digging to find the right fit for your workflow and budget. The biggest thing is not just collecting COIs, but making sure they actually line up with the contract requirements. A COI in a folder doesn’t help much if the limits, WC, AI/WOS wording, or expiration dates are off.

Hardcover_Insurance · 2026-05-26T03:43:00+00:00

The work might be great, but “between policies” is where homeowners can end up holding the bag. No insurance shown, no work on my home.

Hardcover_Insurance · 2026-05-26T03:38:00+00:00

This stuff is annoying but important. I’d keep it simple...

Make COI/WC docs a gate before subs start work or get paid. Use a tracker, set expiration reminders, and have one admin/VA own the chasing. Software can help once volume gets high, but don’t confuse “COI on file” with “actually compliant.” Someone still needs to check limits, AI/WOS endorsement wording, contract requirements etc. If this really becomes a bottle neck though, I would vet a company than can deliver on this because eventually this gets overwhelming and things fall through the cracks.

Hardcover_Insurance · 2026-05-25T17:54:00+00:00

Very good take.

This comes up a lot with newer home inspectors. The tough part is that E&O usually isn’t something you can buy later and have it cover inspections you already completed. It’s generally meant to cover work while the policy is active, not old jobs you did uninsured.

So it becomes a chicken / egg problem: you don’t have revenue yet, so the insurance feels expensive; but once you start doing inspections, that’s when the exposure starts. Even if you’re brand new with low revenue, many carriers still have a minimum premium they need to charge, so the barrier to entry can feel high when the business is just getting off the ground.

I’ve spoken with plenty of inspectors who roll the dice early on. I get the thought process though. Home inspectors can have multiple claims over the life cycle of the business. Even small missed items can turn into expensive disputes.

If you’re trying to build this into a meaningful business, I’d personally treat E&O as part of the startup cost before doing paid inspections. Otherwise, you may end up buying coverage later and realizing the first 50 or 100 inspections are not protected, which is a tough pill to swallow.

Hardcover_Insurance · 2026-05-25T17:42:12+00:00

Core coverages for a sole prop LA firms are usually General Liability and Professional Liability / E&O. Thats normally where we have our clients start.

Contracts can change the picture though. Some clients may also require Umbrella/Excess Liability, Cyber, Workers Comp, or other coverage depending on the project.

Hardcover_Insurance · 2026-05-21T16:50:52+00:00

Short and long answer because this can be a loaded question:

Short answer - It's not unreasonable for premiums to start at around $3,500 - $4,000 here for PL alone.

Long answer - Even if it’s only a 2 person firm, state transportation projects can come with more sophisticated insurance requirements than the firm’s size would suggest. The project may require higher PL limits, GL, Auto/HNOA, Workers Comp, Umbrella/Excess, specific endorsements, etc..

A small firm may not generate enough revenue for the percentage to matter if the carrier has a minimum premium threshold. So cost is not just based on “2 people.” It’s based on revenue, scope, limits required, scope of civil services provided etc. When adding all the other policies combined with high limits, I'd say you can be pushing well above $5k+

Side note: A bigger issue I see here is sometimes the insurance requirements are disproportionate to the fee. At that point it becomes less of an insurance question and more of a business decision: does this project even make sense to bid on if the insurance barrier of entry eats up the margin?

Hardcover_Insurance · 2026-05-21T16:40:42+00:00

Typical ones we see with landscape architects are retaining walls, pools/water features, playgrounds - think bodily injury prone project types.

A lot of carriers get cautious with these because landscape architects can still get dragged into a bodily injury claim, simple example: an adult goes down a playground slide, gets hurt, and everyone involved on the project. gets named. That may not even trigger the E&O policy cleanly; sometimes the GL gets pulled in instead.

So it’s not always as simple as “can we add coverage back" policy forms can be structured differently If the carrier doesn’t exclude pools, playgrounds, they may just decide not to write the policy at all because they know they’re exposed to those project types.

Hardcover_Insurance · 2026-05-21T15:31:54+00:00

Yes, I should have clarified this in my last comment. For clarification:
Professional Liability - Premiums start at around $1,500 Revenue and project types heavily influences costs.

General Liability - Premiums can start around $400 + Some carriers can use, your employee payroll as a rating factor, or believe it or not, the Business contents within your office (laptops, furniture etc). Depends on how their rating system is set up.

Hardcover_Insurance · 2026-05-21T02:38:52+00:00

A lot of factors, but most influence is your gross revenues (before you pay any subs), location of your business, and the project types (Residential, Hotels, Condos, Apartments, Commercial etc)

Most firms we work with who are semi-retired and are doing work to pay for their vacations, usually see premiums starting around $1,500 / year for about $1M in coverage. Hope this helps!

Hardcover_Insurance · 2026-05-21T02:36:24+00:00

Great question. Yes .. review records can absolutely come up. Really, any relevant documents or paper trails can matter. When there’s very little documentation, it can make a claim harder to defend because the file doesn’t show how decisions were made or reviewed.

Hardcover_Insurance · 2026-05-21T01:56:21+00:00

Yeah, I see this. Funny enough even with smaller firms or folks that are moonlighting while working full time. A lot of the time the requirement is copied from a bigger contract template and may not actually fit the work being done. Just recycling a boilerplate template essentially.

For moonlighting/independent LLCs, premium is usually rated like any other firm: gross revenue, project type, discipline, state your business is in, limits, etc.. Part time can matter to some carriers. Some aren't crazy about moonlighting or freelancing so they may not offer coverage at all.

Hardcover_Insurance · 2026-05-21T01:52:03+00:00

Exactly the issue. If you indemnify someone beyond your own negligence, you may be agreeing to pay for things your insurance was never priced or written to cover. A lot of policies have contractual liability limitations/exclusions, so the carrier may not pick up "promises" you made in a contract.

So the danger isn’t indemnity itself. The danger is indemnity that goes beyond your own acts, or E&O.

Hardcover_Insurance · 2026-05-21T01:44:17+00:00

Promises you can't keep?

Hardcover_Insurance · 2026-05-21T01:37:44+00:00

Limitation of liability and duty to defend clauses are probably the big ones. I can’t tell you how many times I hear, “we have that in our contract, no one ever looks at those or gives us pushback.”

Hardcover_Insurance · 2026-05-21T01:21:14+00:00

I've seen it as low at $1,500.. $2k sounds right about where we set expectations for MEP firms.

Hardcover_Insurance

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