OOAK Mastermind III
Castelfalfi, Tuscany · August 21–23, 2026
The strongest competitive advantage in business is who and what you know that your competitors don't. Spend three days at a 5-star private resort in Tuscany with a handpicked group of founders building 7 to 9-figure brands. Expect world-class speakers, top-notch experiences, and real connections with founders on the same path as you.
Why this exists
The unlock isn't on the internet
Your biggest competitive advantage will always be who you have access to that your competitors don't. That next-level insight, the new unlock that breaks your ceiling, only gets shared between operators in the same room. Three days with hand-selected founders and a handful of high-level guests, all building brands at scale.
The unlocks, resources, and connections made here compound for the rest of your career. The only way to stay ahead is to be in the room with the people doing the same. We want to create that room.
Where it happens
The Location
Castelfalfi
Tuscany, Italy
The Estate
A luxury restored medieval village sits on 1,100 hectares of vineyards and olive groves, and the environment alone makes you think bigger. It's a place that resonates with the finer things in life, where the right people meet and the right conversations happen.
Private Stay, All-Inclusive
Your own 5-star room for three days. Meals, drinks, airport transfers. Everything's on us. Nothing on your mind except the business and the people around you.
The Experiences
The best conversations happen when nobody's trying to have one. A wine tasting at sunset, a gala dinner under the castle walls, and long terrace nights. The room never stops working.
The Reset
Time to think bigger. Three days off the grid in a medieval Tuscan estate, with no Slack, no fires to put out, no calls, just the space to think clearly about what actually matters in your business and connect with others doing the same.
The Experience
The Event
Application OnlySurrounded by the 1%
Every seat is earned through application and track record. We invite high-level guests, business owners you'll recognise, and the founders beside you run 7 to 9-figure brands. These are operators usually behind a paywall, a waitlist, or a closed door. For three days, they're at the same table as you.
KeynotesWorld-Class Speakers & Guests
The OOAK founders, our high-level partners, and a handful of invited brand owners who've built at the highest level. Every keynote and fireside is built around moves you can use, not theory you'll forget.
The Q4 Playbook
Every attendee walks away with the OOAK Q4 Playbook on top of everything shared live during the three days. It lays out the exact moves that will drive the biggest season in OOAK history, the one we're realistically projecting at $35M USD across the portfolio. Take it back to your team and walk them through how we prepare Q4 in detail.
Live Problem-SolvingThe Hot Seats
Structured working sessions where the room digs into the real problems you're facing. Your business, your numbers, solved live with founders who've been there.
Other brands in the room
Built for a lifetime of impact
Network
Relationships with other e-com founders that pay off for years, supplier intros, agency referrals, JV deals, and calls you actually take.
Learn
In-person keynotes, firesides, and open Q&As with founders who've solved your exact bottleneck, CAC, retention, ops, hiring. No theory, real skin in the game.
Speak in person
The best connections are made offline, during activities, fine dining, and our gala. Direct, face-to-face access to high-value operators, the conversations that never happen over a cold DM or a Zoom call.
The Investment
Step into the room
OOAK Mastermind III
The 3-day Mastermind€12.500
What's included
- 3-day luxury stay in a private 5-star resort
- Fine dining, drinks, activities covered
- Direct access to the 1% in DTC ecommerce
- Multiple 9-figure guests, keynotes and firesides
- The OOAK Q4 2026 Approach & Playbook
Application-only. Book a call and we'll walk you through the room and whether it's the right fit, before the seats are gone.