A two-year family voyage that changed business views

Caspar Craven’s big bold goal caused an upheaval of business and family life for the better

Gettyimages 697853664 WEB
Cherry Reynard
Published: 26 Nov 2021 Updated: 13 Apr 2023
10 Caspar 01

Caspar Craven’s big bold goal caused an upheaval of business and family life for the better: a thriving business and sailing round the world with family.

Motivational speaker, entrepreneur and adventurer, Caspar Craven controversially dismisses the concept of a work-life balance. “You have one life. You have a work team and a home team and you neglect either at your peril.” He can comfortably claim to have supported both, having built a thriving business, but also spent two years sailing round the world with his family.

Caspar would go one step further arguing that the experiences on one side can be invaluable in the other. The drive to go on this great adventure with his family pushed him to make his business better, to find a way it could run without him, while his sailing adventure taught him lessons about motivation and teamwork he would never have learned in an office. It is the lessons he learnt from both sides that now inform his career as a speaker and author.

The seeds of this multi-faceted career were sown early. Caspar grew up in Devon, close to the beach. His first business was catching crabs and lobsters and selling them on the beach. This included an early lesson in branding, after he developed his trademark ‘crabs for sale’ T-shirts. He even got a taste for the import/export business when he started exporting crabs to Spain. “It was summertime stuff, but it gave me a taste.”

Early years

Nevertheless, his early career followed a conventional path – university and then three “painful” years in accountancy. After struggling through and qualifying, he took some time out before coming back and joining the corporate finance division at KPMG: “I learnt a bit about doing deals and fund raising. The 1990’s were a useful time to be doing this sort of thing – there were a lot of fast-growing technology companies and I got to meet lots of technology founders.”

Caspar was making his way up the ladder when he went to the London Boat Show. Without thinking too hard, he signed up as a reserve for a round-the-world sailing race. Ten days later, he was called up: “The race brought together ordinary people to do an extraordinary thing. The crew came from all walks of life, all cultures.” While KPMG thought well of him and welcomed him back, the trip had set his sights in a different direction. He decided it was time to branch out on his own. His first venture was building online social networking sites.

He launched dating sites, which operated a little like Facebook. He raised some angel financing and built the site, but it was too slow-moving. He incubated the site, took a finance director’s job and considered his options.

His next venture was a data analytics business, but he was hatching an altogether bigger and more exciting plan – to travel round the world with his wife and children. He found that this personal goal gave his business new momentum: “When I first had the idea, my business was ticking along, but not taking off. It gave me a deadline – five years to get it together. I needed to get the business into a shape where it could run without me.” He built an amazing team of people and ended up selling it when he was halfway round the world.

Life is an audacious daring adventure

Caspar and his wife knew they wanted to do something life-changing with their children. In making their decision, they did an exercise called ‘deep listening’. Caspar says: “This aims to really understand what’s driving someone. From this exercise, we found common threads between us on travel and adventure.”

Caspar’s background naturally led him to sailing, but Nichola had only been on a boat twice and had been seasick both times. Undeterred, they initially thought they would sail round the Mediterranean, but then the project “grew arms and legs.”
“We created a vision statement and stuck it to our kitchen wall. We wanted it to be a life-changing experience for us and the children.”

He admits there were many, many reasons not to do it. “Safety, Nichola couldn’t sail, we didn’t have a boat, we had no medical training, we’d need to home-school the children, we didn’t have enough money!”

Their solution was to plan forensically. “My wife was a barrister, I was an accountant. Neither of us were in the habit of throwing caution to the wind, so we spent five years in scenario planning. We had back-up plans on back-up plans. We thought of every single risk and we had a strong sense of self-preservation.”

They finally set sail in August 2014 and stayed on their 53 feet sailboat until June 2016. During that time, he says they had “magical lifechanging experiences, moments that will last forever.” Even now, he says, the trip lines their family home with pictures of it on their walls.

“It was scary and magical and the most amazing bonding experience. When I look at how the kids are developing, I think we planted so many seeds in that time. My son has a love of the natural world and languages and I believe it comes from that time. He built a real sense of compassion.” His book about the experience ‘Where the Magic Happens’ tells the story of how the trip grew from the seed of an idea, to a hugely ambitious goal, to making it happen in practice.

The return

By the time he came back, the sale of his business together with the successful launch of two other ventures had turned their finances around.

“Thinking about how to make the business work without me meant that I took my ego out of the business. It enabled the business to grow properly.” This is one of the key lessons he now shares with people in his talks and business books.

He has loved this latest change of career: “I’ve never done anything quite so meaningful. I can see how it changes people’s lives.” He helps individuals and organisations identify ‘Big Bold Goals’ and has developed best practice for teamwork within organisations. Part of his premise is that businesses need to put ‘humanity’ back into the workforce.

This has become particularly relevant during the pandemic. Businesses have been forced to take account of their employees’ lives away from the office. As the world reopens, the hope is that businesses put people first. Not only is it the compassionate thing to do, but it is single best way to achieve audacious goals. Caspar certainly hopes so: “Those businesses that are all about the numbers with people as the afterthought? They’ve had their day.”

Return to Enterprise Homepage


This article was previously published on Smith & Williamson prior to the launch of Evelyn Partners.