Adventure Trips are small-group expeditions that combine real adventure — skiing, sailing, hiking, cycling — with deep, unfiltered conversations about designing a life on your terms. You don’t just learn the Freedom Stack. You live it.
When you’re pushing your limits on a mountain or sailing through open water, the pretense drops. The conversations that happen in those moments are different from anything that happens in a conference room.
Each expedition is structured around the Freedom Stack framework. You experience what Adventure Freedom, Geographic Freedom, and Relationship Freedom actually feel like — not as concepts, but as reality.
Eight people maximum. Application-based. Curated for people who are already building something — and who want to think more clearly about where they’re going. The group is half the value.
Each trip is curated for a small group of high performers. Spots are limited to eight people and filled by application. Trips sell out quickly — get on the list early.
Four days skiing the best terrain in Colorado, with mornings on the mountain and evenings around the fire working through the Freedom Stack together. Designed for people who already know how to ski and want to think differently about how they’re building their life.
Five days sailing the Apostle Islands on Lake Superior — one of the most dramatic freshwater sailing environments in the world. No experience required; Ned is at the helm. Days on open water, anchorages in sea caves at dusk, evenings working through what geographic freedom and risk tolerance actually mean in your life.
Three days on a section of the Appalachian Trail — America’s most storied footpath, where the simplicity of the next white blaze creates a rare mental clarity. No cell service, no agenda beyond the trail. Evenings around camp working through the Freedom Stack with people who understand the weight of a life well-built but not yet fully free.
Five days riding the Ozark trail systems — Arkansas has quietly become one of the premier mountain biking destinations in the country, and almost nobody outside the sport knows it yet. Mornings in the saddle through ridge and river terrain, evenings working through the Freedom Stack around the fire.
Each expedition has its own character, but every trip follows the same intentional rhythm.
These trips are not for everyone. They’re designed for a specific kind of person — and the group experience depends on the group being right.
Trips are all-inclusive once you arrive. You book your flights; we handle everything else.
Investment varies by trip — typically $3,500–$6,500 per person all-inclusive, depending on destination, duration, and accommodations. Exact pricing is shared in the application process. Not included: flights to the destination city.
Apply to Find Out More →Replace placeholders with real photos from actual trips as you run them. Nothing sells this experience better than authentic imagery.
Experiences from people who’ve been on the trips.
Applications are reviewed within 72 hours. If there’s a good fit, we’ll schedule a short call to discuss which trip is right for you and what to expect.
All applications receive a personal response — not an automated confirmation.
If there’s a potential fit, we’ll schedule a 20-minute call to discuss the trip, the group, and whether this is the right timing for you.
The application is the start of a conversation, not a commitment. You’ll have full information before any payment is made.
If you’re interested in more than one expedition, note that in the form and we’ll discuss fit for each.
If yours isn’t here, send it directly through the application form.
Skill requirements vary by trip and are listed in each trip description. Some trips (sailing) require no experience; others (skiing, biking) require an intermediate level. You’ll never be left behind — the group moves together.
Every participant is reviewed by application. Groups are curated for professional level, values alignment, and the diversity of experience that makes the conversations interesting. We don’t just fill seats.
All trips are designed for solo participants. Most people come alone — that’s part of what makes the group dynamic work. You’ll leave with real relationships.
Apply for the trip you’re most interested in and note your availability. We can add you to a waitlist for sold-out trips or keep you informed about future expeditions.
Each trip has different demands. Details are listed per-trip. Generally: you should be active, healthy, and capable of sustained physical activity. We’re not competing — we’re exploring.
Full details are shared during the application process. Generally: 50% refund 60+ days before departure, no refund within 30 days. Trip insurance is recommended for all participants.
Trips are designed for individuals. Couples occasionally attend the same trip, but the evening sessions work best when people can speak candidly — and that’s easier when you’re not attending as a pair.
Yes. The goal is to run 4–6 expeditions per year across different activity types and locations. Join the Freedom Stack community or submit an application to stay informed about new trips as they’re announced.