What do you do when the storm hits?

Do you cling to what was—or boldly redefine what could be?

Caspar Craven knows what it means to navigate the unknown.

He’s sailed around the world. Twice. Once in a gruelling yacht race as team leader. And again—just a few years later—with his wife and three young kids under 10.

But he’s not just an adventurer. He worked at KPMG, is also a serial entrepreneur, a former CFO, and a leading voice on what it really takes to achieve Big Bold Goals—not through spreadsheets and pressure, but through people, purpose, and the power of bold conversations.

Welcome to episode 105 of TIE Unearthed.

In this episode, Caspar joins me to talk about the deeply human side of leadership.

We explore how constraints—whether in the middle of the ocean or in the boardroom—unlock creativity and resilience.

Why real leadership means getting out of the comfort zone and going deep.

And how our identity, fear of failure, and unwillingness to have uncomfortable conversations are often the biggest barriers to change.

Caspar shares what happened when he led a team with a “drive hard, win fast” approach—and how it ended in burnout and dysfunction.

And he explains why it’s not enough to aim for results—you need to create a culture where people feel valued, understood, and safe to contribute.

We talk emotions. Vision. Reinvention. AI. And how the best leaders aren’t afraid to rethink the rules—and lead from a place of depth, not just direction.

So if you have ever felt stuck, overwhelmed, or unsure of how to lead when the path isn’t clear, this one is for you.

👉 Tune in, and ask yourself:

What bold conversation are you avoiding?

And what might be possible if you had it?

🎧 So grab that favourite beverage, or throw on those running shoes, and get inspired by Caspar.

👉 Don’t forget to share your thoughts on the episode, leave a review, and subscribe!

If you'd like to stay updated on future episodes and other inspiring stories from TIE, join our newsletter ⁠⁠[⁠here⁠⁠⁠].

If you would like to order my international bestselling book Return on Humanity: Leadership lessons from all corners of the earth, you can do that ⁠⁠⁠[here⁠⁠⁠].

If you'd like to learn more about Caspar, check out his site [here]