A ‘Rivendell’ Retreat | Lisbon, Portugal | 21-23 October 2025

The AI Reckoning

Reinvent your business, your leadership, and yourself in the age of AI—before AI reinvents you.

A transformational retreat for leaders of consequence

You’ve already achieved what most leaders only dream of. But AI is accelerating everything—and it’s triggering a deeper reckoning.

This isn’t just about automation or tech. It’s about who you’ll need to become.

What will leadership really mean in the age of AI?
How must your focus evolve—and how will you rise to meet the moment?

To lead in 2025 and beyond, you’ll need:
✔️ A bold reimagining of what you’re building
✔️ An executive team that's thinking exponentially, not linearly
✔️ The courage to let go of what worked yesterday—so you can lead what’s next

This is your moment to decide:
Will you lead in the age of AI—or be led by it?

Welcome to The AI Reckoning

Where you'll confront the biggest disruption of our lifetime and reimagine your future – at every level.

This isn’t a product demo. It’s a crucible.

A high-flame environment where you’ll confront the identity shift your next chapter demands, the strategic reinvention your business can’t delay, and the culture that will define whether you scale—or stall.

  • You'll craft a bold reinvention plan for your business, leadership, and focus.
  • You'll reimagine your leadership identity and leave clearer, more confident, and ready to navigate the turbulence and opportunities of the AI era.

If you want to ignite your next chapter with clarity, power, and ambition—
this is the room you need to be in.

Who should attend

This retreat is exclusively for pioneering CEOs and visionary entrepreneurs driving bold change. Only those ready to lead at a higher level and inspire unparalleled results need apply.


The retreat will be a great fit if you are:

  • Championing a bold, expansive vision for yourself and your organisation.
  • Committed to making huge progress – even if it's uncomfortable.
  • Looking to learn from inspiring peers who are equally ambitious and forward-thinking.

What to expect

In this transformative 48-hour retreat, you’ll engage in carefully designed sessions that blend strategy, leadership, and personal transformation. Here’s what awaits you at The AI Reckoning:

Kickstart Session

Before the retreat, engage in an optional invigorating group call that paves the path for the empowering journey ahead. This session is curated to ensure you embark on this programme with clarity and vigour.

Peer Group Interactions

Step into the world of our elite Rivendell community, where you’ll meet highly-successful maverick leaders running substantial, impactful businesses. Iron sharpens iron, and sparks will fly as you engage on a deep level with these inspiring individuals.

Strategic Reinvention

We’ll guide you through the reinvention of your business strategy, leadership approach, and team standards for the AI era. You’ll face the real questions:

What’s the boldest version of what you’re meant to build?

What’s the leadership stance required to make that inevitable?

Where must you stop tolerating mediocrity—in yourself or others?

Immediate, Lasting Impact

You’ll leave with breakthroughs in your leadership approach, practical tools to navigate the uncertainty of the technological transition ahead, and a renewed sense of clarity and purpose to achieve your most ambitious goals.

Deep Leadership Coaching

The retreat is more than strategy. It’s about becoming someone new. You’ll go deep into your own operating system—so that what you create externally matches the boldness of what’s possible internally.

Rest and fun

Breakthroughs come in the chat, the relationships and the space to simply think. We make time for all of that, too.

An exceptional experience

This will be our seventh Rivendell retreat. These are transformative environments that have been the catalyst for top leaders who lead some of the world’s most innovative, impactful organisations. Here, you don’t just strategise; you become the leader who will deliver your next-level goals.

What do CEOs, entrepreneurs and industry leaders say about their experience with Rivendell? Here’s how it’s helped them achieve exponential growth and transformation.

Everyone in the group is extremely successful and at the top of their game. I could write a whole essay about my learning from those few hours that we had last week!

RIVENDELL PARTICIPANT

Safe environment for "eureka" moments

If you've got a spark of curiosity, and you want to learn, and you're open minded enough to put yourself in an environment where you're exposed to those new opportunities, then Rivendell is ideal for you. It's a very safe environment to experience those "eureka" moments. I've enjoyed engaging with other business leaders, learning from them and helping them develop... and being coached by Richard throughout. And I've found some significant business development opportunities in speaking with other members!

Bob B.

We’re executing a bigger vision

Rivendell has really opened my eyes to what is truly possible for the business, and now my team and I are in execution mode delivering on that.

Rivendell member

Challenged me to drive growth and ambition

Richard challenged me to really get out of my comfort zone, think long and hard about what gets in my way, and focus on what I really should be doing—driving growth, ambition, and the future direction of the organisation. This Rivendell retreat has given me the energy, drive, and ambition to come away to actually deliver on the promises you make to yourself as a leader.

Chris Barnes

An unbelievable gathering

An unbelievable gathering of peers (founders and CEOs). Thanks to the guidance, the methodology and Richard's creativity, we went deep and addressed our common challenges. I strongly recommend Rivendell to any CEO who wants to become a better leader for their team and their family.

Armand A.

Produces exponential impact

Rivendell has helped me in two big ways. I’m able to get qualified input from experienced people on my toughest business challenges. And it's has pushed me to get a much clearer picture on my strategy and my goals. I've had so many practical insights about my business, to solve specific problems that I can't discuss with with many people. And I've got a much clearer picture on my strategy and my goals. I would recommend Rivendell to senior leaders who want to make 10X impact instead of incremental impact.

David Engel

A life-changing opportunity

Initially I wondered how I could contribute to such an advanced group. However, it's been a transformative experience that far exceeded my expectations... an extraordinary opportunity to engage with CEOs at the pinnacle of their respective fields and committed to making a positive global impact. The beautiful retreat location was the perfect backdrop for reflection and breakthrough thinking. Rivendell has been pivotal in reshaping my leadership and has profoundly influenced my thoughts on amplifying my impact. I'd recommend it to any CEO who is eager to explore new ways of leading. It’s a life-changing opportunity to connect, grow, and reset the bar.

Abe Klassen

Brought clarity and a strategic vision for growth

During the Rivendell retreat last week I gained clarity, a strategic plan, and a clear description of the attitude needed to succeed. He helped me bring together all the different pieces into a long-term vision and identify key opportunities for growth. Highly recommended for any top leader approaching an important moment in their professional journey or facing some significant decisions within their organisation.

Christopher Traggio

A real depth

I have found the Rivendell experience to be incredibly valuable to help me reflect on who I am as a leader and how I can improve the use of my skills and capabilities, and it's given me the opportunity to interface with other CEOs. We've had a fabulous time sharing experiences with each other, and I'm learning a tremendous amount, not only from Richard but also through the individuals in the Rivendell program. There’s a level of depth that frankly I haven't gotten in any other program that I've been involved in. 

Scott Puopolo

Brought clarity, challenge, and ambition

This last retreat has changed my perspectives, given me challenge, and been a lot of fun. Most of all, my thought process on the journey that I am on—and that we are on—is crisper, cleaner, and more ambitious than ever before. If you're on a journey with a destination that you believe is transformative for your industry, sector or yourself, you’ll come out with a clarity of thought and energy that will be magnified.

Nick Hale

On another level

Rivendell is on another level compared with my local YPO group!

Rivendell Participant

Incredible calibre of people

Rivendell is a really fulfilling experience. I've done quite a few different professional development events, but the thing that really stood out to me here is the intermingling of personal and professional development. I have a notebook full of new ideas! The calibre of the other participants has been humbling and it feels like a privilege to really be among such an esteemed group of people and peers.

Kelly Manthey

Sharpened my thinking

Rivendell has really helped me sharpen what I think is our distinctive value proposition. It's energised me to think about the coming months as we're looking at our growth plans. It's rare to get to speak in an in a way that's off the record, professional, but also very collaborative with executives who've led a variety of businesses, and to be able to work through challenges that are not easy to voice in other contexts.

Talal D.

Clarified my mission

I recommend Rivendell for leaders who are conscious, thoughtful and want to do something big and important in this world. It gave me the breathing room I needed to contemplate the future, clarify my mission, and get clear on my purpose. With Richard's guidance and the group support I’ve created new strategies for achieving my objectives.

Chintan Panchal

Another league

The recent Rivendell retreat has been the most exciting two days of my life: I've gained so much self insight, as well as insight from others who've gone through similar things to me. Thanks to the coaching from Richard, it has been a tremendously, tremendously positive and exciting experience. What I've experienced [in Rivendell] is another league compared with programmes I've experienced before.

Mikael Sandberg

A fantastic opportunity

It was fantastic to get the input of other highly experienced leaders, and I learned a lot about myself through the process. Rivendell is a safe space where you can be honest and open about the issues you're facing. It gave me the opportunity to question my values and motivations, and learn how to approach situations in a more strategic, powerful way.

Danny Keating

Inspired insight and long-term transformation

Working with Richard has been inspiring—he has a gift for drawing out valuable insights and helping leaders see long-term. I’ve come away from the last Rivendell retreat with a totally different approach to operating in my business, thanks to the exercises he led and his ability to create a deep and meaningful space for transformation.

Alexandre Dufour

Space to think and to grow

Rivendell is an environment where everyone is ready to go deep from the outset. It’s inspiring to spend time with ambitious peers who want to get better and learn as much as they can about themselves and others. Rivendell has given me space to think, be challenged, and process all of this. I’d recommend the experience to leaders who are feeling stuck or lonely and want to grow.

Steve Rowbotham

7 figures of value

Last week at the retreat with Rivendell I got really a clear path to massively impact the work that we've been doing. We've been implementing changes even this week and can already see seven digits worth of value being added to the business from some decisions that came out of that time away.

Toby Alcock

A 48-hour deep dive into leadership & strategy

The retreat will be held 21-23 October 2025. Here’s a high-level overview..

Day 1: Challenge

Tuesday 21st October

  • 2pm-6pm: Immersion! We’re going to take you very deep, very fast. Be ready to be challenged and pushed beyond your comfort zone.
  • 7pm: Informal evening of connection and fun.

Day 2: Stretch

Wednesday 22nd October

  • 9-5pm: Strap in! This is where the rubber hits the road. Get ready for a powerful day where we'll provoke your ideas, mess with your thinking, and challenge your limiting beliefs.
  • 7pm: Dinner: You will be our guest at the Rivendell dinner, where there’ll be a few surprises in store!

Day 3: Action

Thursday 23rd October

  • 9am-12pm: Final session and action planning.
  • 12pm-2pm: Optional lunch and debriefing.
  • Plan to depart no earlier than 12pm. To maintain the energy and focus of the event, you will not be admitted into the final session if you need to leave before 12pm.

Venue

We’ll be staying in the beautiful Vila Galé Collection Palácio dos Arcos hotel, just outside Lisbon, Portugal and about a 30 minutes car journey from the airport. 

It’s the perfect place to step back, rethink and become the magnetic leader who can deliver on your most audacious goals.

Reserve your place today

There are just 15 spaces at the Rivendell “AI Reckoning” Retreat. Priority is given to members of the Crucible, with a limited number available for other extraordinary leaders ready to experience this transformative environment.

So, if you’re ready to join other visionary leaders who are setting the pace for the next generation of industry innovation, here’s how to register:

  1. Purchase your spot using the form below
  2. Fill in a brief onboarding questionnaire
  3. We’ll get you everything you need to magnetise your people to your mission

Any questions? Reach out to us for a private conversation about whether it's a good fit for you.

Note: If for any reason we determine that you’re not a fit for this elite group of leaders, you will be refunded in full within 72 hours of your application. Also, please note that travel and accommodation costs are at your expense.

“The AI Reckoning”

A Rivendell Retreat

SOLD OUT

Meet your guide

Richard Medcalf
Founder

Richard Medcalf describes himself as "what you get if you were to put a McKinsey consultant, a slightly unorthodox pastor and Freddie Mercury into a blender!"

Richard is the trusted advisor to elite CEOs and founders facing The 10X Reckoning—the moment they realise they’re stuck in their current success, playing too small, or moving too slow on their vision.

His 1:1 clients include billion-dollar CEOs, tech unicorn founders, an Entrepreneur of the Year, and an Olympic medallist—leaders determined to break out of incremental progress and create their life’s greatest work.

He’s the author of Making TIME For Strategy and the upcoming The 10X Reckoning, and has an insatiable love for spicy food and the electric guitar.

Learn more about Richard...

Reinvention isn’t optional anymore.

But doing it with power, clarity, and joy? That’s rare.

Join us for The AI Reckoning. Forge your future before the future happens to you.

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