What the Woods Taught Me About Building a Team

When I was twelve years old, I joined a two-week leadership training program at a sleep-away camp. No phone. No internet. Just a group of kids, some canoes, backpacks full of gear, and a lot of things that did not go the way we planned.

Canoes tipped. Food ran out. It rained for days. I got seriously sick on one of the trips and made it through anyway.

I did that program twice as a kid, at twelve and again around thirteen or fourteen. Then I worked at the camp as a counselor through college. Then in my early twenties I ran those programs myself. I took kids out into the woods and onto rivers and watched them figure out, the same way I had, what they were actually made of.

I never connected any of this to cityHUNT until recently.

A Different Kind of School

There is a lot of conversation now about grit. What it is, whether you can teach it, whether people have enough of it.

I do not know the whole answer. But I know what those two summers did to me. When you go days without working technology, when you have to solve food and weather and navigation as a team, when things go wrong in the middle of nowhere and quitting is not actually an option, something gets built in you. Not just toughness. More like trust in the process, even when the process is cold and wet and nobody is sure where the campsite is.

A writer I have been reading lately, Pixie Light Horse, said something that stayed with me: leaning into comfort sometimes happens at the expense of being present. I keep coming back to that. In a world that works hard to smooth everything out, presence is what gets traded away. And presence is the only thing that actually connects people.

The Tipped Canoe

Being an entrepreneur is uncomfortable at a lot of moments. There have been stretches in cityHUNT’s 25-year history, after 9/11, during the 2008 crash, through COVID, where I did not know if we were going to make it.

Looking back, I think the reason I could stay steady enough to work through those periods is that I had already, at age twelve, learned what it felt like to be cold and tired and lost and still keep moving. The woods did not teach me that everything would be fine. They taught me I would figure it out either way.

That is a different thing. It turns out it matters a lot. It shows up in the same way dyslexia shaped my thinking. Both built a kind of resourcefulness that does not show up on a resume but does show up under pressure.

A Program in Disguise

I started cityHUNT in my NYU dorm room in 2001. A scavenger hunt pub crawl using Polaroid cameras. For 25 years I have been building it into something that now operates in 250+ cities, pulling teams out of conference rooms and into the streets together.

I always understood the mission from the inside. Get people into a shared challenge. Something real. Watch what happens between them.

What I had not traced until this year was where that instinct came from.

I can trace it to specific moments now. Canoes tipping in bad weather and nobody walking away. Kids showing up terrified on day one and leaving knowing they could handle something genuinely hard. All those times a group of strangers in an uncomfortable situation chose to help each other instead of checking out.

cityHUNT was always a leadership training program in disguise. It just took me 25 years to realize I had been running the same program since I was twelve.

Conclusion

It was never about making things easy. We were building something that had to actually mean something.

Twenty-five years later, that is still the test. If an experience does not require something of you, it probably will not give you anything back.