The first ever Nail it, Scale it, Sail it Experiential Bootcamp - by invitation only!
Action Learning at its Best !
Welcome to the Nail it, Scale it, Sail it Experiential and Train the Trainer Bootcamp – Master and Connect in Paradise
A transformative five-day executive course combining academic excellence with experiential learning in the breathtaking landscapes of the Azores.
More details coming soon - Summer 2026 | São Miguel Island, Azores, Portugal
Dear NSS alumni,
If you are reading this, it means you are part of the Nail it, Scale it, Sail it community and are ready for the next adventure! Congratulations!
Many of you have asked us for a deep, hands-on experience—one that allows you to apply the NSS framework in new ways, explore additional case studies, diagnose challenges within your own organizations, and master the “Train the Trainer” methodology for coaching and certification.
We listened. And we are thrilled to introduce the first-ever NSS Experiential Bootcamp—a by-invitation-only, immersive leadership retreat designed for a selected group of alumni of programs led by Prof. Loredana Padurean and Prof. Charlie Fine. (Note: this is not an MIT or Northeastern program - at least not for this first edition). Spaces are limited, make sure you secure your interest soon. See below the interest registration page.
Please do not share this page outside of the NSS community. This event is not open for the general public. However, we are welcoming members or partners from your current organization, if they share an appreciation for the NSS framework and are willing to attend a 3h zoom pre - bootcamp exposure session.
First thing first - Why the Azores?
We searched the globe for the perfect location—one that embodies the Nail it, Scale it, Sail it spirit and São Miguel Island in the Azores stood out.
Known for its safety, cleanliness, stunning landscapes, organic local food, and easy navigation, the Azores is the ideal setting for our journey. While some physical activities are involved, this isn’t “Survivor”—no peak fitness required! This is NOT A LUXURY destination, but a down-to-earth experience with good people and great food.
The town of Povocao, San Miguel Island, Azores
Jungle-like landscapes (minus the mosquitos!)
Breathtaking mountain peaks for the ultimate (but very doable) challenge!
Deep blue Atlantic waters for a fun sailing adventure that might even show us dolphins and whales if the weather permits!
Program Schedule*
Five Days of Transformative Learning
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Theme: Welcome & Setting the Stage
🔹 2:00 PM - 4:00 PM | Opening Session - Bootcamp overview, objectives, and expectations. Group introductions & icebreakerUnderstanding the NSS Learning Journey – From Jungles to Mountains to Oceans - a recap and group discussions of your experience with the framework.
🔹 4:30 PM - 6:00 PM | Train the Trainer (TTT) Session 1 – The Foundations - What makes a great NSS trainer?
Understanding adult learning principles
How to facilitate executive education effectively
Creating engaging, interactive learning environments
What’s different about training founders, executives, and teams?
🔹 7:00 PM - 8:30 PM | Welcome Dinner at Restaurant Riquim & Networking
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Theme: The Startup Jungle – Mastering Agility & Problem Solving
🔹 Morning | Class Session
(1) Understanding the “Nail It” Phase
Case studies: How early-stage startups or initiatives succeed or fail
Applying the “hacker mindset” to business operations
The role of Nailers in an organization
(2) Train the Trainer (TTT) Session 2 – How to Train for the “Nail It” Mode - Topic: How to train founders & startups in the Nailing stage
Learning Outcomes:
How to teach agility & problem-solving to early-stage teams
Facilitating fast decision-making in environments of high uncertainty
How to run an interactive case study & discussion
🔹 Afternoon | Jungle Adventure at Salto do Cagarrão
Picnic lunch at Forest Recreation Reserve of Agua Retorta
Outdoor jungle experience (problem-solving in uncertainty, agility training)
Group Reflection
🔹 Evening | Free Time & Reflection
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Theme: Growth & Execution – Building for Scale
🔹 Morning | Class Session
(1) Understanding the “Scale It” Phase
Case studies: How companies successfully scale operations.
The 10 tools for Scaling (Processification, Culturalization, Automation, etc.)
The role of Scalers & Organizers in company growth
(2) Train the Trainer (TTT) Session 3 – How to Train for the “Scale It” Mode - Topic: How to train teams for operational growth.
Learning Outcomes:
How to teach structured growth & process-building
Facilitating workshops on scaling operations & leadership
Handling resistance to process & structure in growing companies
🔹 Afternoon | Mountain Hike at Sanguinho
Lunch at Sanguinho Village
Physical endurance challenge & metaphor for structured scaling.
Group Reflection
🔹 Evening | Free Time & Networking
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Theme: Leading for Long-Term Success & Market Expansion
🔹 Morning | Class Session
(1) Understanding the “Sail It” Phase
Case studies: How mature companies sustain innovation
The role of Sailors & Stabilizers in organizations
Navigating change, competition, and uncertainty
(2) Train the Trainer (TTT) Session 4 – How to Train for the “Sail It” Mode - Topic: Teaching long-term strategy & adaptability
Learning Outcomes:
How to facilitate strategic thinking & corporate innovation
Using data-driven decision-making in training
How to coach executives on navigating complex markets
🔹 Afternoon | Sailing Experience at North shore
Lunch at Restaurant Caldeiras
Leadership at sea: Navigating complexity, adaptability, and vision
Group Reflection
🔹 Evening | Celebratory Dinner at Sabores da Terra – Everyone’s Invited!
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💡 9:00 AM - 12:30 PM | Train the Trainer (TTT) Final Certification & Teach-Backs - Topic: Assessing and certifying NSS trainers
🔹 Learning Outcomes:
Participants deliver mini-training sessions to test their knowledge.
Receive feedback from NSS faculty & peers
Certification Panel: Trainers are evaluated on content mastery, facilitation, and coaching skills
🛫 1:00 PM | Departure from the hotel
*Agenda Subject To Change
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This is not a lecture—it’s a transformational experience and a unique learning experience. This 5-day immersive program blends leadership development, strategy, adventure, and team-building in a dynamic, experiential format. Each day mirrors a stage of the NSS journey—jungle, mountain, ocean—culminating in a high-impact coaching session to help you certify as an NSS trainer and mentor.
A Unique Learning Experience
Tentative Details
Dates: Summer 2026 - details will be provided soon
Duration: 5 days
Location: São Miguel Island, Azores, Hotel do Mar - Povocao
Cost: 5’500 usd - includes the hotel room in single, 3 group lunches, 2 group dinners and local travel but not the flights.
Getting There: Ponta Delgada Airport
Direct flights to the Azores available from the USA, Canada, the UK, and several European countries. São Miguel is just 4.5 hours from London, 5 hours from Boston, and 2.5 hours from Lisbon. Airlines like SATA/Azores Airlines, TAP Portugal, Ryanair, TUI, Delta, and more connect this stunning destination to the world.
You will be responsible for booking your own flight to the island. The hotel for the program is Hotel Do Mar - we will book the rooms for you.
Discover São Miguel Island, Azores
São Miguel Island, the largest in Portugal's Azores, is a nature lover's paradise with scenic hikes, dramatic coastlines, and volcanic landscapes. Located 1,643 km from Lisbon, it’s a serene European escape.
Video Credit: cinexs-ch