The first ever Nail it, Scale it, Sail it Experiential Bootcamp - by invitation only!

🚀 Welcome to the Nail it, Scale it, Sail it Experiential and Train the Trainer Bootcamp – Master and Connect in Paradise

August 17-21 2025 | 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 maximum 20 select 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.

🌿 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!

Azores is one of the safest, cleanest, and most stunning destinations in the world. With organic local food, no natural predators, and an easy-to-navigate infrastructure, the Azores is the ideal place for this journey. The experiential part of the adventure will require some physical activities but this is not “Survivor” so don’t worry if you are not at the peak levels of your fitness! ;-) This is NOT A LUXURY destination, but an honest, no fuss, down to earth, good people and good food culture!

Tentative Schedule (subject to change)

📍 Day 1 | Sunday, August 17 – Kickoff & Connection & Train-the-Trainer Foundations

Theme: Welcome & Setting the Stage

🕑 2:00 PM - 4:00 PM | Opening Session - Bootcamp overview, objectives, and expectations. Group introductions & icebreaker

• Understanding 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 | Group Dinner & Networking

📍 Day 2 | Monday, August 18 – Welcome to the Jungle! (Nail It Phase)

Theme: The Startup Jungle – Mastering Agility & Problem Solving

🌿 7:00 AM - 1:00 PM | Jungle Adventure

• Outdoor jungle experience (problem-solving in uncertainty, agility training)

📚 2:00 PM - 4:30 PM | Class Session – 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

🎤 4:30 PM - 6:00 PM | 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

🍽 Evening | Free Time & Reflection

📍 Day 3 | Tuesday, August 19 – Scaling the Mountain! (Scale It Phase) - Theme: Growth & Execution – Building for Scale

🏔 7:00 AM - 1:00 PM | Mountain Hike

• Physical endurance challenge & metaphor for structured scaling.

📚 2:00 PM - 4:30 PM | Class Session – 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

🎤 4:30 PM - 6:00 PM | 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

🍽 Evening | Free Time & Networking

📍 Day 4 | Wednesday, August 20 – Sail Ahoy! (Sail It Phase) - Theme: Leading for Long-Term Success & Market Expansion

⛵ 7:00 AM - 1:00 PM | Sailing Experience

• Leadership at sea: Navigating complexity, adaptability, and vision

📚 2:00 PM - 4:30 PM | Class Session – Understanding the “Sail It” Phase

• Case studies: How mature companies sustain innovation

• The role of Sailors & Stabilizers in organizations

• Navigating change, competition, and uncertainty

🎤 4:30 PM - 6:00 PM | 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

🎉 7:30 PM | Celebratory Dinner – Everyone’s Invited!

📍 Day 5 | Thursday, August 21 – Train the Trainer Certification & Next Steps

💡 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

So, are you ready to join an exclusive 5-day immersive experience designed for NSS alumni who want to deepen their expertise, earn their train the trainer certification, and solve real business challenges—together? What’s in it?

🔹 Master the NSS Framework – Deep-dive into new case studies, tools, and strategies - beyond what you learnt in the previous programs.

🔹 Earn Your NSS Trainer Certification – Develop coaching & facilitation skills in an innovative framework.

🔹 Solve Your Organizational Challenges – Tap into the power of collective intelligence to find actionable solutions for your company.

🔹 Build a Powerful and Meaningful Network – Connect with high-caliber peers in an exclusive, intimate setting.

🔹 Experience the Extraordinary – Learn while adventuring through jungles, mountains, and oceans in the stunning Azores.

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.

💡 Why we believe this approach works:

✅ Progressive Learning – You will build your learning, problem solving and training skills daily, rather than cramming it into one day.

✅ Immediate Application – You will apply what you learn in real-time through experiential learning, case studies and interactive discussions with peers.

✅ Trainer Readiness – By the last day, they are already familiar with training methodologies, making the certification more effective.

I’m Interested!