Caspar Craven

Charting Success - 8 Steps to Navigating a Winning Team

New image Caspar May 2019

Book Caspar Craven today!

Caspar has over 30 years’ experience in building teams to make things happen.  Starting as an entrepreneur at the age of 14, he has built and led teams in global corporations, start-up businesses, struggling businesses and high growth businesses.

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

Along the way he’s built multiple successful businesses from scratch and sold one for a 7 figure sum whilst sailing the Pacific Ocean.

Caspar launched his 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, he 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.

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

In 2001 he returned to entrepreneurial life as an e-commerce entrepreneur. Over the following 15 years, he raised money for, built, grew and sold businesses primarily in the technology sector. He’s made mistakes. He’s fallen over. He got up again and carried on. He’s had some great successes and some failures.

In 2009, together with his wife, he created a plan to sail around the world with their three young children and spent the next 5 years planning how to make things happen. In 2016, he successfully completed his second circumnavigation, this time with his family having experienced amazing highs and agonising lows thorough this 7-year life changing voyage from idea to completion.

Since returning he continues to build amazing teams having launched new businesses and also planning and undertaking challenging sailing adventures.


Caspar spoke at our annual user conference in California. 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 a…

— Dan Rodrigues – Founder and CEO, Kareo

I recently engaged Caspar to speak at our Datacore Sales Kick-off in Malta. The feedback from the team was overwhelmingly positive. Caspar provides a balance of practical advice and inspiration, the delivery is authentic and entertaining. I highly recommend Caspar.

— Amanda Bedborough – Senior Vice President, Operations EMEA at DataCore

Caspar is a consummate professional and one of the safest pair of hands on the speaking circuit.  

He did a superb job at our annual awards for 470 of the small business and investment community. An insightful, genuine and inspirational storyteller that was bang on message for the evening.

— Guy Tolhurst – Small Business Champion, mentor and leading practitioner on SME and Alternative Investment