INDEX / COMMUNITY
Founder Mastermind Retreat Network
A structured, recurring off-site mastermind program for early-stage founders with professional facilitation, curated cohorts, and experiential activities.
▶ WATCH THE SOURCE SEGMENT — Keeping it Real with Danny Trinh01 THE IDEA
Greg describes a years-long practice of renting a house in LA with 6-7 entrepreneurs, hiring a professional moderator and chef, and running structured sessions alongside fun bonding activities (shooting guns, dinners, etc.). The format combined ~50% structured peer advisory time with unstructured bonding, and he credits it with spawning real companies like Breather and Flow Water. He explicitly says he wants to bring it back and invites listeners to reach out if interested.
The business model is a premium retreat operator for founders: curate cohorts of 6-10 high-trust builders, charge a per-event fee (or membership), handle logistics (venue, chef, facilitator, activities), and deliver the low-judgment peer environment that founders can't get from VCs, teams, or Twitter. Revenue comes from ticket sales, annual memberships, or corporate sponsorships. This is distinct from generic entrepreneur conferences because of small group size, professional moderation, and off-site immersive format.
02 THE NUMBERS
$150K – $800K
$15K + 200h
$8K + 60h
2/10
7 · GROWING →
community curation, event logistics, facilitation or moderator management, sales/outreach to founders, brand building
03 THE VERDICT
There is clear, validated demand (Greg ran this for years and it generated real outcomes), the market is underserved at the intimate/experiential tier, and the unit economics can work well with even 3-4 retreats per year at $2,000-$4,000 per head. The main risk is operator credibility and network bootstrapping, but anyone with a modest founder network can launch a pilot with minimal capital.
04 THE FIELD
- YPO (Young Presidents' Organization)est. 1950STEADY · ADDED 2026-06-07
CATEGORY LEADER IN CEO PEER GROUPS
Global peer network for CEOs with forum groups, but very formal and expensive (~$5k+/yr dues).
- Entrepreneurs' Organization (EO)est. 1987STEADY · ADDED 2026-06-07
LARGE ESTABLISHED PLAYER
Peer network for entrepreneurs with chapter-based forum meetings; broad but less curated for early-stage builders.
- Hamptonest. 2022GROWING · ADDED 2026-06-07
FAST-GROWING MODERN ENTRANT
Curated community and mastermind for founders doing $1M+ revenue; modern brand, waitlist-driven.