It started 32 years ago in insurance claims — crawling under damaged cars, negotiating with body shops, figuring out what happened and what it was worth. Eleven years at Progressive, starting in 1993, then eleven more at American Family, where I kept solving technology problems until they stopped asking me to fix things and put me on the Innovation team — building tools like Claims Copilot, designing social analytics for investigations, researching vehicle telemetrics before most people had heard the word.
That got me recruited to Automatic, a startup building connected car technology. Sirius XM acquired them, changed the product, and eliminated what I was doing. So I went back to running agencies, pursued MBA studies at Edinburgh Business School, and spent years doing digital marketing for local businesses and nonprofits.
The whole time, the same problem kept showing up: smart business owners making important decisions based on gut feel because nobody had shown them what the data actually said.
Then I got diagnosed with ADHD at 50, and everything clicked. The decades of patterns made sense. I built The Firehose Method — an AI-powered system for managing the cognitive overload that comes with ADHD. It worked. People paid for it within 48 hours.
Here's what I realized: every overwhelmed business owner has a version of the same problem. Not ADHD necessarily — but the information overload, the decision fatigue, the feeling that you should be holding everything in your head and you can't. I built tools to help me see my own chaos clearly. It turns out those same tools help businesses see theirs.
That's what Gray Owl Group is. Not another marketing agency. Not an AI hype shop. A consultancy that helps you see what you've been missing — built by someone who had to solve that problem for himself first.
Gray Owl Group is based in Burlington, Wisconsin — right at the intersection of Racine, Walworth, and Kenosha counties. We work with local businesses who want sharper insight into their own operations, and we serve clients nationally who need the same thing at a larger scale.
Small enough to pick up the phone. Capable enough to build what enterprise consultancies charge ten times more for.
Burlington isn't just where we're headquartered — the Southern Lakes area is our home. Guy is Chairman of the Elkhorn Joint Review Board and an Elkhorn Police and Fire Commissioner. He previously served on the Round Lake Area Schools Board of Education in Illinois and is a director at PM&L Theatre in Antioch. This is a place we're invested in, not just located in.
No pitch decks. No pressure. Just a conversation about what's going on in your business and whether we can help.