MOST FOUNDERS DON’T GET TO
CHOOSE HOW THEIR STORY ENDS.
They wait too long. Or sell too early. Or walk into a process thinking they’re ready. Then they find out, painfully, that they’re not.
I’ve seen it happen to smart people. Hell, it almost happened to me.
This retreat exists because I don’t want that for you. I want you to exit on your terms, with your eyes open, knowing exactly what you’re walking into.
WHAT A 19,000-FOOT CLIMB TEACHES YOU ABOUT SELLING YOUR COMPANY
Sounds like a stretch, right? But here’s what I’ve learned from doing both:
Preparation beats ambition. You don’t summit because you want it more. You summit because you trained, acclimated, and made smart calls along the way. Same with exits. The founders who “win” aren’t the most aggressive. They’re the most prepared.
You find out fast if your team can handle pressure. When conditions deteriorate, you see who you can trust, and who folds. Same in a deal process.
Knowing when to turn back is just as important as pushing forward. The summit isn’t the point if you don’t make it home. Same with your exit, it isn’t just the close, it’s what you walk away with.
This retreat puts those lessons together in a way you can’t get from a consultant or a book.
THE EXIT PROBLEM
You’ve built something real. But when you start thinking about selling, the questions pile up:
- What’s this thing actually worth? Not what you hope, but what a buyer would pay.
- Can the business run without you? Or are you the bottleneck everyone pretends doesn’t exist?
- What would due diligence uncover? The gaps you’ve been meaning to close but haven’t?
Most founders don’t have honest answers. And by the time they’re in a process, it’s too late to fix them.
THE LEADERSHIP PROBLEM
Here’s the other thing nobody tells you: how you lead under pressure determines your outcome.
- When things get uncomfortable, and they will, do you push through and make smart decisions?
- Do you trust your team? Do they trust you?
- Can you stay disciplined when the stakes are highest?
The mountain shows you exactly how you operate when it matters. That’s information you need before you walk into a deal room.
HERE’S HOW IT WORKS.
PHASE I: BEFORE THE CLIMB
Strategic Exit Assessment
The retreat starts before you get on a plane.
You and I have a private, confidential conversation about your exit readiness. No sugarcoating. We look at your business the way an acquirer would:
- What’s your company actually worth today vs. your walk-away number?
- How deep is your leadership bench? Can this run without you?
- What would due diligence uncover?
- Are you building something buyers fight over, or pass on?
You land in Ecuador with clarity on where you actually stand.
PHASE II: CLIMBING SCHOOL
Cayambe, Ecuador — 19,000 ft
Then we go to the mountain.
Cayambe is Ecuador’s third-highest peak. Real glacier travel. Real mountaineering. This isn’t a hike. It’s not Everest either. Serious enough to mean something. Achievable for anyone willing to do the preparation. Your safety is addressed by professional, certified mountain guides.
You’ll learn:
- Rope work and glacier travel
- Risk assessment under real conditions
- Decision-making when things deteriorate
- How you operate under pressure, and with a team
The goal isn’t just the summit. It’s what the mountain shows you about yourself.
PHASE III: AFTER THE CLIMB
Your Exit Roadmap
When you come down, we’re not done.
The final session translates what you experienced into a concrete plan:
- Leadership shifts needed over the next 12-36 months
- Strategic priorities that actually move valuation
- What’s driving you, what’s holding you back, and what to do about it
You leave with a roadmap. Not a theory. A plan to exit on YOUR terms.
WHY THIS MOUNTAIN?
Cayambe isn’t the tallest mountain I’ve climbed. But it’s the right one for this.
Serious enough to teach you something — 19,000 feet with real glacier travel
Accessible enough to be practical — arrive, train, acclimatize, and summit in a focused timeframe
A real introduction to high-altitude mountaineering — skills that carry over to everything else
Challenging. Immersive. Achievable.
THE INVESTMENT:
$24,000. Everything is included except flights to Ecuador.
What’s included:
- Private strategic exit assessment (before you arrive)
- Complete mountaineering training with professional guides
- All lodging, meals, and ground transportation in Ecuador
- Post-climb integration session with your 12-36 month roadmap
- Ongoing access to me for follow-up conversations
No hidden costs. No upsells.
Each retreat is limited to 8 founders. Small enough for real strategic work. Small enough that I know your business by the time we’re done.
THIS IS FOR YOU IF…
You're thinking seriously about an exit.
Maybe 3-5 years out. You want clarity, optionality, and control over what happens next.
You value preparation over winging it.
You know the founders who get the best outcomes start early.
You're willing to be tested.
Physically and mentally. You want to know what you’re made of!
THIS IS NOT FOR YOU IF…
You want a vacation with business content sprinkled in
You prefer broad discussions over focused, high-stakes problem solving
You’re not willing to train, prepare, and do the work
FAQ
Do I need mountaineering experience? No. Education-first. You should be in decent shape and willing to train, but I started endurance sports at 40 with zero athletic background. Preparation matters more than experience.
What if I’m not sure I want to exit yet? That’s exactly when this matters most. Founders who get the best outcomes start 3-5 years before they’re ready.
How physically demanding is this? Challenging but achievable for motivated adults who put in the work. A physical training plan and consultation with an expert is included.
Is this group or private? Both. Strategic sessions are private. The mountain is shared with a small group of peer founders.
What happens after? You leave with a roadmap and ongoing access to me. Many founders continue into advisory relationships, but no pressure.
Are more details availble? Click here for a detailed description with daily itinerary.