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Adventure Club: a group of hikers climbing a green mountain valley

We’ve got something for you…

We have loved having you in Adventure Club and are excited to present you the programs for 2027.

Since you’re an alumni you have two to choose from:

  1. Adventure Onward (Alumni only)
  2. Adventure Club 2027 (New cohort)
Option 1

Adventure Onward (Alumni Only)

One Big Adventure: Grand Tetons (Aug 25–28)
Two City Meet-Ups: Miami (Feb 4) NYC (May 6)
Business Forums & Expert Coaching

What is included…

The Big Adventure: Grand Teton

Coach Chris is taking you across the Teton Crest Trail. Granite peaks rising straight off the valley floor, glacier-fed lakes, alpine meadows: Grand Teton from the inside. We’ll cover 39 point-to-point miles and nearly 10,000 feet of gain in one push. Make no mistake: this is NO JOKE. Coach Chris will make sure you’re ready. All inclusive.

City Meet-Ups

Two chances to reconnect with the crew in person. Adventure Club team plans a group dinner and activity for each meet-up. The rest of the weekend is yours to explore the city. Lodging not included.

Beyond the Adventures

  • The business and coaching you’re used to, plus access to new experts
  • Monthly business forums with Jon Carroll
  • Adventure coaching with Coach Chris: he’ll prepare you for Jackson Hole
  • Monthly office hours with experts: small-group sessions with Coach Chris, Jon Carroll, and new experts in AI, social media and wellness

Investment: $16,000 ($23,000 value)

Option 2

Adventure Club 2027 (New Cohort)

Wellness & Business Retreat: Rome, GA (Jan 12–14)
Big Adventure #1: Keys Kayaking (Mar 15–18)
Big Adventure #2: Cactus 2 Clouds (May 18–20)

What is included…

The Kickoff Wellness and Business Retreat

Jesse hosts the kickoff at his property in Rome, GA.

Before you take on anything hard together, you get to know who you’re doing it with: every member shares their lifeline, their biggest personal and business moments.

It’s a wellness retreat only Jesse knows how to throw: saunas, cold plunges, breathwork, private chefs, and time off the grid. You’ll leave knowing your crew and feel refreshed.

Big Adventure 1: Keys Kayaking Adventure

Crystal-clear blue water, mangroves, tropical islands, and white sand beaches: this is your playground as you kayak through the Florida Keys. The route takes you way off the typical path, to parts of the Keys most people never get to experience.

You’ll spend your days on the water, lunches on the beach and your evenings enjoying what you’ve earned: group dinners and relaxing nights.

No experience needed. Coach Chris will have you adventure-ready.

Big Adventure 2: Cactus 2 Clouds

One of the biggest single-day climbs in the U.S… close to 11,000 feet of gain over 14 miles, from the desert floor to the 10,834-foot summit of San Jacinto Peak.

In one day, you’ll cross terrain you’d normally drive hundreds of miles to see. You start among the cactus, climb through rocky canyons into cool pine forest, and finish looking out over the entire Coachella Valley.

It’s hard, and that’s the point. This is the day you’ll look back on whenever you need proof you can do something hard. You will earn the relaxation in Palm Springs afterwards.

Beyond the Adventures

  • The business and coaching you’re used to, plus access to new experts
  • Monthly business forums with Jon Carroll
  • Adventure coaching with Coach Chris: he’ll prepare you for Key West and Palm Springs
  • Monthly office hours with experts: small-group sessions with Coach Chris, Jon Carroll, and new experts in AI, social media and wellness
  • $5,000 in free resources created by the experts

Alumni Only Pricing: $30,000 (Normally $38,000)