The No Small Talk Hike
For founders and people who think too much about the big questions. No "so, what do you do?" No elevator pitches. No weather talk. We'll spend a few hours walking in the woods, in pairs that rotate along the trail, with one question per leg of the hike. The questions are the kind you usually only get to at 1am with a close friend:
- What are you building, and what would you lose if it worked?
- When did you last change your mind about something that mattered?
- What do you believe that most of your peers would disagree with?
- Is ambition a virtue, or a very respectable form of avoidance?
- What would you do if you knew you couldn't fail, and what if you knew you couldn't be seen?
How it works
- We meet at the trailhead and get a short briefing and the first question.
- You walk with a partner for about 20 minutes, then we rotate.
- Phones stay in pockets. Photos at the summit are fine.
- We finish with a group debrief at the top, and optionally a drink or coffee afterward.
Who it's for Founders, operators, and builders who want conversation with some weight, and anyone who reads philosophy, argues about it, or just likes thinking out loud. You don't need a company or a reading list. You do need to be comfortable with silence and with questions that don't have tidy answers. The details
- When: Sunday 11th October at 10am
- Where: Cold Spring, New York
- Distance: 2 hour hike
- Bring: Water, comfortable shoes, and something honest to say
- Group size: Capped at [20] so everyone gets real conversations
- Cost: Free
