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How a $30,000 Gap Led Me to Build ClaimOwl

Kevin Fleming
Kevin Fleming Founder, ClaimOwl
I never planned to build an insurance technology company. I'm a software developer. But when our home was damaged, I learned something that changed my perspective entirely: most homeowners have no idea what their repairs should actually cost.

It started with a pipe

Our dishwasher supply line failed while we were at work. By the time we got home, water had been running for hours. The hardwood flooring was buckled. Water had traveled under the cabinets, into the dining room, and soaked the subfloor.

The insurance company sent an adjuster. He walked through the kitchen, took some photos, and a week later we got an estimate. It seemed reasonable at first. I didn't know enough to question it.

The $30,000 difference

Through research and a lot of conversations with contractors, I started to realize how much was missing from our estimate. The subfloor replacement wasn't included. The cabinets were priced as stock when ours were semi-custom with dovetail drawers. The continuous hardwood flooring in the dining room wasn't scoped at all, even though it was the same floor with no transition strip.

Overhead and profit was missing. Mold assessment was missing. Appliance disconnect labor was missing. Code-required GFCI upgrades were missing. Contents pack-out, permits, matching requirements for the adjacent rooms. All missing.

When we added everything up, the gap between what the insurance company initially offered and what the repairs actually cost was over $30,000. We eventually recovered most of it, but it took months of back-and-forth.

The real problem

The thing that frustrated me most wasn't the money. It was that I had no way to know what I didn't know. The estimate was full of line items I couldn't evaluate, industry terms I didn't understand, and pricing I had no way to verify.

Terms like "ACV," "O&P," and "like-kind-and-quality" aren't designed for homeowners. They're designed for industry professionals talking to each other. And the process assumes you'll either accept the first number or hire an expensive public adjuster.

I kept thinking: there has to be a better way. A way for regular homeowners to understand what their repairs should cost without needing a professional license or spending thousands on a consultant.

Building ClaimOwl

I'm a developer. So I built it.

ClaimOwl uses AI to analyze photos of property damage and identify the items that are most commonly undervalued or left out of insurance estimates. It checks for material quality, code requirements, matching rules, and dozens of commonly omitted line items.

Then it translates everything into plain language. No jargon. No confusing line item codes. Just clear information about what your repairs should cost at current market rates, so you can make informed decisions about your claim.

What I believe

I believe homeowners deserve to understand their own insurance claims. Not just the final number, but what's in it, what's missing, and why it matters.

I believe the information gap between insurance companies and homeowners is the real problem. Not bad faith. Not fraud. Just a massive knowledge asymmetry that costs regular people real money.

And I believe technology can close that gap. Not by fighting insurance companies, but by giving homeowners the information they need to ask the right questions.

That's what ClaimOwl does.

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Kevin Fleming