Ep. 64: Caspar Craven - Sailing Around the World With A Family


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Sometimes, when I have conversations with people about some of the amazing things my guests have done, I hear a common refrain. In fact, I sometimes think the same things – they are inspiring and instructive stories, but they do things that I cannot quite do because they “don’t have [insert obstacle, constraint, complication]”. One of the things mentioned is a family – or more specifically, the responsibilities and constraints that having a family entails.

Meet Caspar Craven. Caspar is an entrepreneur and an adventurer. He challenges conventional thinking. He has run and sold companies, competed in round-the-world yacht races and (here’s the family point), he sailed around the world for two years with his wife and three children – aged 9,7 and 2 at the time.

This all started with a realisation that he wasn’t spending enough time with his family as he pursued the demanding career of an investment banker. What started as an idea borne out of a conversation eventually became reality. Caspar joins me to talk all about it.

In this episode, we explore:

  • Caspar’s background;
  • Life at the extremes;
  • Practicalities of sailing around the world:
    • Financial;
    • Family commitments – e.g. his kids’ schooling;
    • Logisitics;
  • The risks associated with this endeavour and how Caspar and his family managed them (e.g. storms, medical emergencies, piracy);
  • Difficult moments / when things go wrong;
  • The importance of values and purpose;
  • Much more!

Show notes:

Caspar’s website

Caspar on:




Pre-order Caspar’s book Where the Magic Happens on Amazon

The Science of Luck by Bong Chandra


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