Steven runs an independent insurance brokerage. One guy, a real book of business, and a Squarespace site that looked like he had signed up for the free trial and never come back to it.
He wanted it to look like a real brokerage. Not a landing page. Not a template with his photo dropped in. A site that felt like it belonged next to the firms his clients might be comparing him to.
That was the brief.
Where it started
The original site was one of those default Squarespace layouts where everything is centered, the font is whatever the platform picked, and the only thing telling you what the business does is a tagline and a contact form. It was not bad. It just looked like a thousand other small business websites.
Before I touched anything in Squarespace, I designed the new version in raw HTML first. Full layout, proper sections, real hierarchy, a color system built around navy and warm gold that signaled trust and professionalism without looking like every other financial services site on the internet. Once the design was where it needed to be, I converted all of it into Squarespace manually.
That process is not fun. Getting a truly custom Squarespace website means fighting the platform at every turn. Every section needed custom CSS. Every spacing decision had to be made twice. But the result was a site that looked genuinely custom, because it was. That is the difference between affordable web design and cheap web design. The price is accessible. The output is not generic.
The thing he had almost built
At some point in the conversation Steven mentioned something he had been thinking about for a long time. A tool that would help visitors find insurance agents in their area, connected to real carrier data, with some kind of intelligent matching built in. He had started sketching it out but never shipped it.
That idea stuck with me.
By the time the project wrapped up, I had built him a version of it. An AI agent embedded directly in the site, built around his specific use case, that he could actually use and continue refining. Not a third-party chatbot widget. Something built for his business specifically, designed to help his visitors find the right coverage without picking up the phone first.
He was able to keep tweaking it himself after delivery. That was intentional. The goal was never to make him dependent on me for every change.
The honest number
An agency would have charged somewhere between ten and fifteen thousand dollars for that project. Custom insurance website design, a full Squarespace rebuild with custom CSS, and a bespoke AI feature built from scratch.
He paid $3,900.
That is not because the work was worth less. It is because I do not have a creative director, an account manager, a project manager, and three developers splitting the invoice. There is one person doing the work, and that person has been doing this long enough to do it fast.
Steven was happy. The site looked like what he asked for. The tool did what he imagined. And he walked away with something most brokers his size do not have.
That is the job.
Work with Matt
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