I landed in Boston with three months in the US ahead of me and a budget that American accommodation prices were about to eat alive. So I put an AI agent to work hunting vans, and a week later I was on a bus to Philadelphia.
Earlier this year I set up a company in Singapore that builds applications for wearable devices. After the CHI conference wrapped up, I had a rare gap in front of me: three months in the United States with no fixed address and a lot of work I could do from anywhere. This series is the story of how that went. It involves a van, a small army of AI agents, a pair of smart glasses, and more Planet Fitness branches than I can count.
A week in Cambridge, and a reality check
I landed on 26 April and went straight to Boston. The plan for the first week was gentle: wander around Cambridge, catch up with friends at MIT, and visit the Media Lab. That part delivered. The Media Lab is one of those places where every corridor conversation turns into a demo, and it was a good way to arrive.
The other thing that week delivered was a spreadsheet-shaped fright. I had budgeted for the US being expensive. I had not budgeted for how expensive. Hostels, cheap Airbnbs, the bottom shelf of the accommodation market: everything I looked at would quietly drain the entire trip fund and give me a bunk bed and a shared kitchen in return.
Somewhere in that week the maths flipped. Three months of the cheapest beds I could find cost more than a decent used van. A van would be an asset I could sell at the end. It would also be a bedroom, an office and a kitchen that moved with me. I have converted and camped out of vehicles before, so this was less of a leap than it sounds. The decision took about a day. Finding the right van took a little longer, and I did not do it alone.
Outsourcing the hunt
Here is the thing about searching marketplace listings for a van: the good ones are gone within hours, and the search itself is mind-numbing. So I did what I have been doing for most repetitive work lately. I built an agent for it.
The brief I gave it was specific: a van, under $7,000 USD, with enough interior height that a six-foot person could plausibly stand, plus a few other criteria about age and condition. Every hour it swept the listings for newly posted vehicles across the East Coast and flagged anything that matched. I was willing to travel to the right van, so the search radius was wide. By the time the right one surfaced, the agent had churned through somewhere north of 3,000 listings that I would otherwise have had to eyeball myself.
While the van agent hunted, other agents handled the logistics of me being a person without a vehicle in a country built around them. Getting between cities meant buses and trains, so I ran agents against Greyhound, FlixBus and Amtrak to find the cheapest sensible routes, and then had them plan the trip around whatever they found. It was also tech week in Boston and then New York, and I fed the full event calendars to an agent that already knew my profile. It came back with a shortlist of which events were worth registering for and where the networking would actually be useful. More on what came out of those events in a later post.
The one in Philadelphia
The van that won was in Philadelphia, and it had a detail I did not know I was looking for: it was previously an accessibility van, which means the floor had been dropped four inches. In a standard cargo van I would be permanently hunched. In this one, at six feet tall, I can stand up straight. That one modification, done years ago for someone else's wheelchair, is the reason the next three months were comfortable instead of chiropractic.
It had room to work, room to cook, and room to sleep without folding myself into furniture. And it was well under budget: $3,400 for a 2007 Ford Econoline E-150, less than half the ceiling I had given the agent. I took the bus down from Boston, looked it over, and bought it.
Those first Philadelphia days set the pattern for the whole trip: work happens wherever there is a seat and Wi-Fi. Sometimes that was a café. Sometimes it was a University of Pennsylvania workshop I had quietly slipped into, listening with one ear while getting things done.
The first week of the trip ended with me owning a van in Philadelphia and a to-do list of everything wrong with it. The next two weeks were spent turning it into a home, with parts arriving at friends' places up and down the coast and a pair of smart glasses doing more of the work than I expected. That build is the next post.
Vanlife with Agents: