Scrappy Founders Go to Hawaii. Season 1 · Finale
12 Scrappy Founders - an outdoor endurance community for founders and investors in the Bay Area.
Season 1 · Finale. The last chapter of our documentary series following a small group of Bay Area founders through a year of outdoor challenges. Yosemite, Tahoe, dirt bikes, the American River. Kauai closes it.
One island. One house. A week to build, explore and get to know each other beyond the usual boring stuff.
We're heading to Kauai for seven nights with a small crew of founders. Work from the villa, disappear into the jungle or spend the afternoon at the beach. Come evening, we're all back at one table cooking dinner together.
The Plan
Seven founders. Co-founders and partners welcome as +1s.
Weekdays: yours. Some of us will be working from the house, some are taking a few days off to explore.
Evenings: group dinners, BBQs, sunsets and local food.
Weekend: handed over to the island. ATV rides, an open-door helicopter flight, jungle hikes, beaches and time on the water. Everything's optional, pick what's on your list.
Stay: seven nights in one villa, individual bedrooms.
Who is this for?
Founders: seed to Series B founders who want a reset, time to build and a few friends who'll still be around after the trip.
Adventure-minded: be ready for a few hours of activity on some days. No pressure to do everything.
Good people: we care about a balanced, welcoming group. Newer to the outdoors? Totally fine!
The Logistics
When: October 28 to November 4, 2026.
Where: Kauai, Hawaii. Direct flights SFO to Lihue (LIH).
Cost: the open room is $2,900 for the week, or $1,450 each with a +1. Flights, food and activities are on you, roughly $2k. Full breakdown here.
What's Included?
Seven nights at the villa.
Breakfasts and snacks stocked all week.
Some group dinners and activities on us.
All the coordination: bookings, permits, transport, guides and gear. Activities are paid separately.
A small film crew will catch a few dinners, the weekend adventures and some conversations on the porch for the documentary. The rest of the week is off-camera.
How to Join
One spot left. Request to join here and we'll set up a 15 min call with the folks who look like a match.
The group is small and we want it to be a fit both ways. Once we've talked, you pick your room on the trip page. +1s welcome.
Partners:
Red Bull Basement helps first-time founders turn ideas into products through mentorship and AI tools.