My Story

I believe in challenging conventional thinking on how leaders and teams become truly effective and create extraordinary results.

I have 30+ years’ experience in building teams to make things happen. Starting as an entrepreneur at age 14, I’ve built and led teams in global corporations, start-up businesses, struggling businesses and high growth businesses.

My experience includes 10+ years in Professional Services including 5 years at KPMG Corporate Finance and several stints as a CFO.

I’ve built a team on a trophy-winning world racing yacht. But my toughest challenge by far was building my family team to sail around the world: with my wife and three children aged 9, 7 and 2.

I’ve built multiple successful ventures from scratch and sold one for a 7 figure sum whilst sailing the Pacific Ocean.

I’d like to share what I’ve learnt so that you can reach your own goals both in business, at work and in your personal life.


My Career Started...


I launched my first business at the age of 14 catching crabs and lobsters and by the age of 16 was exporting 1/2 tonne of crabs a week to Spain.

Realising that catching crabs wasn't going to make an impact on the world, I went to University and for the next 8 years worked in the corporate world - first as a Chartered Accountant and then as an Investment Banker at KPMG.

Watch Captain on the Worlds Toughest Yacht Race

Watch Captain on the Worlds Toughest Yacht Race

In 2000 I signed up for the Worlds Toughest Yacht Race, the BT Global Challenge and joined Yacht Quadstone as the youngest crew member onboard. After winning trophies around the world and building a team as Watch Captain I returned to KPMG to run a Technology and Telecoms team.

In 2001 I returned to entrepreneurial life as an e-commerce entrepreneur. Over the following 15 years, I've raised money for, built, grown and sold businesses primarily in the technology sector.

I've made mistakes. I've fallen over. I've got up again and carried on. I've had some great successes and some failures. 

In 2009, my wife and I hatched a plan to sail around the world with our young children and spent the next 5 years planning how to make things happen. In 2016, we successfully completed our circumnavigation having experienced amazing highs, having to make heart-wrenching decisions and agonising lows on our 7-year voyage from idea to completion.

I'm on a mission now to be a truly inspiring leadership and team building speaker, giving actionable advice on how to achieve amazing results both professionally and personally, changing lives for the better.

26 - The Craven family arriving in Panama copy.jpg
Caspar spoke at WPPStream Africa - Incredible insight, guidance and that rare quality of openness to sharing his story with others. He is a brilliant speaker, author and handled the flow of conversation with a group in a most constructive way. Superb human, inspiring.

— Juliana Rotich - Venture Partner at Africa Tech Ventures

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