Winter Retreat: Santa Teresa, Costa Rica
Tickets include round-trip airfare between Santa Teresa & San Jose, taxi fare, 6 breakfasts, 6 days of snacks/drinks, 6 dinners, ATV rental, Equestrian tour, Yoga/Surfing instruction, & Private boat charter
This is not a conference. It’s not a networking event. And it’s not another executive offsite built around conference rooms and PowerPoint.
We’re bringing together a small, carefully selected group of CEOs and founders for several days in Santa Teresa, Costa Rica - one of the world’s increasingly coveted destinations for entrepreneurs, creatives, athletes, and high-profile leaders seeking something beyond the traditional luxury resort experience.
Santa Teresa is a place where the boundaries between adventure, wellness, and extraordinary living tend to disappear. Its remote Pacific coastline, world-class surf, jungle landscape, and understated luxury have made it a favored hideaway for prominent entrepreneurs and celebrities. Jack Dorsey, the billionaire cofounder of Twitter and Block, has a home next door, adding to the mystique of a community known for privacy and a distinctly independent spirit.
THE EXPERIENCE
The agenda will balance meaningful time together with the freedom to experience Costa Rica on your own terms.
Morning wellness & reset
Start the day with yoga, movement, meditation, or simply coffee overlooking the Pacific. There will be time built in to slow down, recharge, and step away from the pace of everyday life.
On the water
Swim in the Pacific, explore the coastline, and venture offshore for snorkeling or scuba diving. For those who want something more active, Santa Teresa's famous surf breaks offer the opportunity to get on a board with local guides.
Horseback riding on the beach
Ride along the coastline with the Pacific beside you - one of those distinctly Costa Rican experiences that feels impossible to replicate anywhere else.
Surfing & adventure
Whether you're already an experienced surfer or have never stood on a board, there will be opportunities to get in the water and experience one of Santa Teresa's defining traditions.
Waterfalls & the jungle
Leave the beach behind for a day of exploring Costa Rica's lush interior - hiking through the jungle, discovering waterfalls, swimming in natural pools, and experiencing the landscape beyond the resort.
Fresh seafood & long dinners
Expect fresh-caught seafood, locally sourced ingredients, exceptional cocktails, and long dinners where the conversation continues well past the point when the plates have been cleared.
THE CONVERSATIONS
The most valuable part of the retreat may happen when nothing is formally scheduled.
Around the table, on the beach, in the water, or over dinner, we'll create space for candid conversations between people who understand what it's like to build and lead companies at the highest level.
We'll explore the questions that rarely make it onto an executive agenda:
What's next? What are you building toward? What have you learned the hard way? Where is AI changing your business? How do you think about capital, people, growth, and life beyond the company?
No keynote speakers. No sales pitches. No forced networking.
Just a small room - and eventually, a very small boat - filled with people worth knowing.
High-Level Schedule Highlights
Wed Nov. 18 - Fly into San Jose, Costa Rica
Thurs Nov. 19 - Private plane to Santa Teresa; check-in to lodging, beach-side cocktails & cookout
Fri Nov. 20 - Executive Mastermind, beach walks, private dinner at luxury villa
Sat Nov. 21 - Waterfalls, ATV Jungle rides, and Beach horseback tour
Sun Nov. 22 - Private boat tour, including scuba-diving, white-sand beaches, and fresh carpaccio.
Mon Nov. 23 - Yoga/guided meditation, co-working at luxury villa, beachside drinks & fresh cuisine
Tues - Nov. 24 - Surfing lessons, co-working at luxury villa, farewell dinner
Wed - Nov. 25 - Travel back to homes