A Year on the Road with AI

I started this trip with a legal pad and a vague plan. Eighteen months later I'm somewhere outside Tucson, Toddy asleep across my legs 70 lbs heavier, laptop open, having a conversation with a language model about whether my business model makes sense.

I suppose that's not the van life content you see on Instagram.

I've been building companies since I was nineteen. Every era has its tools fax machines, then email, then apps, now it,s platforms. AI is the first tool thats felt like a collaborator instead of a calculator. Not because it's sentient. Because it's always there, it doesn't get tired, and it doesn't judge you for thinking out loud at 11pm in a Walmart parking lot in Nevada.

My first real use after deploying AI on 11k end users on a top five financial comapny was just journaling. It was by accident at the time. I'd ramble into a voice note, paste it into ChatGPT, and ask it to help me figure out what I was actually trying to say. Turns out I had a lot to say. Turns out most of it was about fear, childhood and hidden memories that I thought were long buried.

What Toddy taught me that AI confirmed

Toddy doesn't care about the destination. He cares about the window being down.

I kept trying to optimize the trip better routes, better stops, better content, better positioning. Toddy kept jumping out of the van and running straight at whatever was interesting right now. This moment. Eventually I stopped fighting it and started building trips that worked like that. Sprint hard on what's interesting. Park the rest.

AI made that easier. I could pick up a thread from three weeks ago and a different conversation and synthesize something useful in fifteen minutes. No notebook to lose, no context lost.

What I actually built on the road

WebToddy an AI consultancy got its first real traction and companion app paradigm while I was parked in Platoro Colrado on a mountain reservior. I took calls from the van. Sent deliverables from rest stops. The irony of selling AI strategy from the Wheres Toddy Adventure Wagon is not lost on me.

Gravitas came together on the east coast , over two days of bad coffee and good thinking. Tax practice acquisition strategy, sketched out with an AI, refined with a human accountant, executed properly. Angel looked t me. We will call it Gravitas!

The Go Toddy book series ten books using Toddy as the mascot for resilience and grit got its first real outline in a campground in Asheville NC. My son Hudson is part of that story. He doesn't know yet how much of it is about him.

The honest part

AI is not magic. It doesn't replace judgment, taste, experience, or the ability to read a room. What it does is eliminate the blank page problem, the context-switching tax, and the loneliness of working alone in a van in the middle of nowhere.

I still get it wrong. I still make bad decisions. I still have days where nothing works and Toddy is the only one who doesn't care.

But I'm building faster than I've ever built. And I'm doing it from the road, which is exactly where I wanted to be.

The next chapter starts when we get home. But honestly — I'm not sure we're going home.