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Caspar Craven - <p>Creator of the Big Bold Mindset® | 2x Round-the-World Sailor | Former CFO (Multiple Exits) |&nbsp;Inspiring Businesses to Achieve Big Bold Goals by Stretching What They Believe Is Possible</p>

Caspar Craven

Creator of the Big Bold Mindset® | 2x Round-the-World Sailor | Former CFO (Multiple Exits) | Inspiring Businesses to Achieve Big Bold Goals by Stretching What They Believe Is Possible

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5.00 of 5

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5 of 5

We recently invited Caspar Craven to speak at the annual user conference for my company, Kareo. Caspar shared the lessons he learned through building a successful business while preparing for an extraordinarily audacious goal to sail around the world with his wife and three young children. It was an inspiring, uplifting, and enriching speech about leadership and life that made a profound impression on our customers, employees, and me. As a member of YPO, an international CEO organization, I've had the opportunity to hear many amazing speakers over the years and I think Caspar is among the best I've seen. I'm a big fan of Caspar and enthusiastically recommend him to leaders in business and community that want to create a unique and powerful experience at their next event.

Dan Rodrigues- Co-Founder and CEO, TebraCo-Founder and CEO

Tebra

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Why book Caspar Craven for your next event

  • Gain practical strategies to lead transformation and shape culture, aligning teams to deliver Big Bold Goals across your organisation.
  • Equip your teams to communicate clearly, stay aligned, and sustain high performance under pressure in uncertain environments.
  • Learn how to move beyond incremental thinking and deliver Big Bold Goals through clear frameworks that drive measurable results.

Non-binding request for Caspar Craven

Big Bold Mindset® creator, global sailor, & former CFO driving transformation

Caspar Craven challenges organisations to rethink what is truly possible. Drawing on his experience as a two-time round-the-world sailor and former CFO with multiple successful exits, he brings a rare perspective on leadership, alignment, and performance under pressure. His Big Bold Mindset® is built on a simple but powerful principle: when goals become bigger and clearer, teams behave differently. They communicate better, stay aligned, and execute with greater focus. Through engaging and practical keynotes, Caspar equips leaders and teams with tools to navigate uncertainty, embrace transformation, and deliver results that once felt out of reach.

 

Caspar Craven keynote speaker

Caspar Craven is known for helping organisations achieve what they once considered unrealistic. As the creator of the Big Bold Mindset®, he focuses on one of the biggest challenges facing businesses today: turning ambition into aligned action. In a world shaped by rapid change, rising expectations, and the growing impact of AI, many organisations struggle to bring their people together around a clear direction. Caspar addresses exactly that.

His approach is grounded in lived experience. Sailing twice around the world, including with his young family, required absolute clarity, shared responsibility, and constant alignment. At sea, there is no room for confusion or competing priorities. The same principle applies in business. When pressure builds and conditions shift, success depends on how well teams communicate, adapt, and execute together.

 

The Big Bold Mindset®

At the centre of Caspar’s work is the Big Bold Mindset®. It is built on the belief that bigger, clearer goals change how people think and act. When teams commit to ambitious outcomes, they move beyond incremental improvements and begin to operate with greater focus and intent.

However, ambition alone does not deliver results. Caspar emphasises the importance of discipline, structure, and culture. His framework helps organisations translate bold goals into practical actions that teams can follow through on. This includes:

  • Creating absolute clarity around direction and priorities
  • Building strong communication habits across teams
  • Aligning individuals around a shared purpose
  • Maintaining performance under pressure and uncertainty

The result is a shift that goes beyond motivation. It changes how organisations operate on a daily basis.

 

From CFO to global sailor

Before becoming a keynote speaker, Caspar built his career as a CFO, leading organisations through growth and multiple exits. This commercial background gives him credibility with leadership teams who are focused on measurable outcomes and long-term value.

Combined with his sailing experience, Caspar brings a perspective that connects strategy with execution. He understands both the boardroom and the frontline. He has experienced what it means to lead when stakes are high, resources are limited, and decisions matter.

This combination allows him to translate complex challenges into clear, actionable strategies that resonate across all levels of an organisation.

 

Leading transformation in uncertain times

Organisations today are under constant pressure to evolve. Whether driven by technology, market shifts, or internal change, transformation is no longer optional. Yet many initiatives fail because teams are not aligned or equipped to deliver.

Caspar’s keynotes focus on closing this gap. He helps organisations:

  • Align leadership and teams around clear, shared goals
  • Strengthen communication to reduce friction and confusion
  • Build cultures that support accountability and performance
  • Navigate uncertainty without losing momentum

His message is direct and practical. It is not about theory, but about what works when it matters most.

 

Book Caspar Craven for your event

When you book Caspar Craven, you bring in a speaker who combines inspiration with practical impact. His sessions leave audiences with a clear understanding of what needs to change and how to make it happen.

He connects with leaders and teams alike, using real stories and sharp insights to challenge assumptions and unlock new ways of thinking. More importantly, he provides tools that can be applied immediately.

For organisations looking to move beyond incremental progress and achieve meaningful results, Caspar Craven delivers a message that drives action. His Big Bold Mindset® equips teams to think bigger, align better, and perform at a higher level, especially when it matters most.

Caspar Craven - <p>Creator of the Big Bold Mindset® | 2x Round-the-World Sailor | Former CFO (Multiple Exits) |&nbsp;Inspiring Businesses to Achieve Big Bold Goals by Stretching What They Believe Is Possible</p>

Customer Reviews

5 of 5

We recently invited Caspar Craven to speak at the annual user conference for my company, Kareo. Caspar shared the lessons he learned through building a successful business while preparing for an extraordinarily audacious goal to sail around the world with his wife and three young children. It was an inspiring, uplifting, and enriching speech about leadership and life that made a profound impression on our customers, employees, and me. As a member of YPO, an international CEO organization, I've had the opportunity to hear many amazing speakers over the years and I think Caspar is among the best I've seen. I'm a big fan of Caspar and enthusiastically recommend him to leaders in business and community that want to create a unique and powerful experience at their next event.

5 of 5

Caspar is an inspiration. His message of being more human and putting people first has definitely changed my management and leadership style. Having #bigboldgoals, focusing on we not me and doing all you can to get rid of those why nots is key to success. Caspar delivered an amazing, inspiring talk to 42 members of our senior leadership team and left them fired up to really deliver big goals.

5 of 5

We were blown away by his charismatic presentation and experience in achieving Big Bold Goals with a human touch. Caspar was exceptional to work with. He hit the perfect balance between strategy and making it real for the team. We loved it!

5 of 5

Thank you so much for such an inspirational session. You challenged us to think Big and Bold, to take extreme ownership as we embark in being an independent company and to be resilient. The feedback from the team was amazing. We loved the provocation and all felt super inspired. Thank you!!

5 of 5

Having very recently booked Caspar for one of my high profile client engagement events, I cannot recommend him highly enough. His talk was extremely engaging and exciting whilst at the same time delivering some key messages on winning teams which were so relevant for the audience. If you want a speaker who will make people listen and engage, Caspar is the one!

5 of 5

I have organised and attended many speaking engagements in the past, but none have come close to being as engaging. Caspar managed to grip the attention of Burberry colleagues from all over the globe with his captivating stories and easy-to-follow practical steps deemed “worth its weight in gold” by the leadership team.

Rated 5.00/5 based on 6 customer reviews

Keynotes

Keynote by Caspar Craven:

Leading Transformation & Delivering Big Bold Goals

Are you facing the pressure to transform but struggling to align your teams and turn strategy into action?

This keynote focuses on what it really takes to deliver transformation. Not just setting direction, but shaping the mindset and culture required to align teams, engage people, and execute effectively.

Drawing on his experience in business and sailing twice around the world, Caspar shows how leaders and teams can stay clear, focused, and aligned when conditions are changing and pressure is high.

Keynote Takeaways:

  • Learn how to lead transformation by aligning teams around a clear and shared direction.
  • Understand how mindset and culture directly impact your ability to deliver change.
  • Discover practical tools to turn strategy into consistent action and measurable results.
Request a quote: Caspar Craven Leading Transformation & Delivering Big Bold Goals

Keynote by Caspar Craven:

Building High-Performance Teams That Deliver Extraordinary Results

Are your teams working hard but not always aligned, or not delivering at the level you know is possible?

This keynote explores what separates teams that are busy from those that consistently perform at a high level. Caspar focuses on the behaviours, conversations, and clarity required to build alignment, strengthen accountability, and ensure teams are working together effectively towards shared outcomes.

Keynote Takeaways:

  • Understand the key drivers of alignment, accountability, and high performance within teams.
  • Improve communication and collaboration to ensure teams work together effectively.
  • Learn how to create teams that consistently deliver extraordinary results.
Request a quote: Caspar Craven Building High-Performance Teams That Deliver Extraordinary Results

Keynote by Caspar Craven:

From Ambition to Achievement: Delivering Big Bold Goals

Are your teams setting ambitious goals but struggling to follow through and deliver?

In this keynote, Caspar focuses on execution. How to move beyond incremental thinking and turn ambition into action. Using the Big Bold Mindset®, he shows how setting bigger, clearer goals changes how teams think, behave, and perform, and what it takes to deliver against them consistently.

Keynote Takeaways:

  • Learn how to move from ambition to measurable and sustainable results.
  • Understand why teams stall and how to maintain focus and follow-through.
  • Discover how Big Bold Goals drive higher levels of performance, engagement, and innovation.
Request a quote: Caspar Craven From Ambition to Achievement: Delivering Big Bold Goals

Keynote by Caspar Craven:

Leadership Under Pressure: Building Resilience to Perform When It Matters Most

How do you and your teams perform when the pressure is high and the stakes are real?

This keynote focuses on leadership in high-pressure environments where clarity and decision- making are critical. Drawing on real-world experiences, Caspar shares how leaders can stay focused, maintain alignment, and lead others effectively when conditions are uncertain and the margin for error is small.

Keynote Takeaways:

  • Learn how to stay clear, focused, and make better decisions under pressure.
  • Understand how to lead teams effectively in high-stakes and fast-changing situations.
  • Build resilience and consistency in performance when it matters most.
Request a quote: Caspar Craven Leadership Under Pressure: Building Resilience to Perform When It Matters Most

Motivational Leadership Speaker on Mindset - Caspar Craven 2024 Showreel: The Mindset for Big Goals

Watch Caspar Craven in action!

Blog posts by Caspar Craven

It Wasn’t the Weather That Needed to Change

It was our first time sailing a boat as a husband and wife team. The end of a long day on the water and we’d arrived at a bustling port rammed with other boats. There was just one berthing spot left. It would have to be in the most awkward place! Right at the far end of a narrow lane lined with boat

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