I started my first business at thirteen—a lawncare company that helped pay for college. Studied Foreign Policy, ran political campaigns, then spent years teaching middle school because I wanted to understand how people actually learn and change.
The last decade has been entrepreneurship. My wife Rachel and I built The Parker Group into one of the region’s top real estate brokerages, then created an entire ecosystem around it—mortgage, insurance, property management, development. Now I’m building Archie, using AI to solve what’s fundamentally broken in residential transactions.
I got obsessed with questions that don’t have tidy answers. I read everything from Spinoza and Jung to contemporary consciousness studies and neuroscience. The thread just kept pulling—one idea led to another, and I couldn’t stop following the connections. I started seeing patterns everywhere—how Frankl’s logotherapy applies to why founders build, how ancient wisdom traditions speak directly to modern meaning-making.
Rachel and I have been partners for eighteen years, and we’ve always operated this way—moving between disciplines, connecting ideas that seem unrelated, having conversations that span philosophy and pragmatism. For three years I wrote a newsletter exploring everything from real estate to technology to philosophy—over 200,000 words trying to make sense of it all. Dot by Dot is where that exploration becomes more focused: meaning, transitions, the messy middle, the big questions that connect us.
I kick off every morning with CrossFit because physical clarity creates mental clarity. We have two kids who graciously tolerate dinner conversations about simulation theory and consciousness.
This project is an attempt to create more of what I love—conversations where ideas collide across disciplines, where people can wrestle with questions that matter. A space for synthesis thinking, where remarkable minds connect not despite their different paths, but because of them.
I have no formal credentials for this work. Just curiosity, pattern recognition, and a track record of seeing connections others miss. Sometimes that’s enough.
