HR & Management

Daredevil entrepreneurs and their extreme ways of unwinding

10 min read

18 January 2017

It’s been said that every entrepreneur is a bit of a daredevil or adventurer – emphasised all the more by the extreme ways these six bosses unwind.

Facebook’s Mark Zuckerberg plans to conquer some form of frontier each year, with 2017 seeing him travel around the United States to meet as many people as possible. But while it’s certainly a hardy challenge, it doesn’t compare to the tasks these daredevil entrepreneurs set out to accomplish.

If you really think about it, entrepreneurship is much like an extreme sport. You need determination, passion and dedication by the bucketload, and it’s all about the luck of the draw – any one economic factor (much like a natural disaster) can prove fatal even if your business is on a roll.

But there are some people that go above and beyond in proving the correlation between entrepreneurship and extreme sports – so we made it our mission to unearth these daredevil business leaders.

1) No hurdle is too high for this daredevil may be a car search platform, but its founder and CEO, Alastair Campbell, is addicted to the sky. On the company’s site, it suggests he was admittedly attracted to the sport due to its perceived risk – and that he wishes he had the power of flight.

“The first jump scared me so much I completely froze,” he said. “If I hadn’t bought ten jumps I would have gone home as soon as I got back on the ground. Getting back in the plane was tough the second time but after that it was nothing but pure adrenaline.”

This experience happened around the same time the company was started, with a 2016 article claiming it helped him get through the stress of starting up shop. “It is the only sport I have done where every bit of focus is on what you are doing. You are not thinking of your website or cashflow. It is so beautiful, exhilarating and adrenaline-pumping that it completely empties your brain and de-stresses you.”

Apparently he now jumps 100 times a year. And in case you wanted to see the daredevil himself in parachuting action, here’s a clip.

2) The digital nomad travelling the globe

Given her love of adventure it’s apt that Amy Truong created travel blog Generic Dreams and travel agency Up and Explore. However, she hasn’t let work bog her down. In fact, by donning the title of digital nomad she sets out to do some daring deeds wherever she can.

In an interview in July 2016, Truong said: “The thing about travelling is that you don’t want to say no to what could be a great adventure. I figured there’s got to be a way to do more of it than just a few weeks out of the year.”

It’s certainly helped her uncover great attractions, helping her befriend those involved with travel destinations and find out those local haunts tourists tend not to know about.

More importantly, it’s given her the opportunity to let inner daredevil shine. She hiked the Stairway to Heaven – a closed off mountain route with danger signs aplenty – and even bribed a few guards to let her traverse an abandoned skyscraper in Thailand.

Read on for the cage fighter and the daredevil supreme

3) Are you ready to rumble?

The Office Group aims to reconfigure the British office, deeming itself the pioneer of the shared workspace – and one of its co-founders has a love of MMA (mixed martial arts).

It’s been said that Olly Olsen used to play football until his knees and ankles felt the strain. But after meeting former cage fighter Charlie Enstone-Watts, he turned his eye to sport once more – and it wasn’t football. Much like Campbell though, the love he now has for MMA didn’t come until he tried it.

“I thought to myself: I can’t even watch it on the telly, there is something about it which upsets me, I couldn’t do it. It was barbaric,” he explained. “I put the gloves on and Enstone-Watts told me, ‘When you are putting your elbow through the jaw, you’ve got to come down on it’. I’m thinking, ‘you’re kidding me? I don’t want to break anyone’s jaw!’ But something just clicked inside.

“Now, after my training sessions I am much more balanced in my decision-making and it has given me a lot of mental confidence, too. Those that doubt are the ones that lose.”

4) The all-time daredevil

What list about daredevil entrepreneurs would be complete without entrepreneur Richard Branson? After all, he’s a big advocate of adventures helping you bounce back after business mistakes.

He said: “The important thing is to take what you have learnt from the experience and apply it to your future ventures going forward. That’s why I will never quit going on daily kiteboard rides. Life is the ultimate adventure and I plan to be pushing the boundaries for many more years.”


This philosophy has led him to attempt breaking the world record for the fastest crossing of the Atlantic Ocean, bungee-jump off a casino in Las Vegas, crash a hot air-balloon and, well, dress up in drag.

He further added in an interview with Adam Toren for the Entrepreneur that the hot-air balloon crash affected his business decisions. “You have to stay calm under fire – and sometimes literally under fire. If you’re facing death, you’ve got two choices: one is curling up and giving up, and the other is fighting to survive.”

Carry on for the Flash of the corporate world and the man who trekked the Antarctic 

5) Do you have the need for speed?

Estate agency Butcher Residential’s principle, Ian Butcher, like the others on the list, has a daredevil at heart. His passion, however, is to burn rubber on the roads.

Butcher, an article claims, has a love for racing – using a Renault 5 GT Turbo to steer competitively on weekends. And of his hobby, Butcher explained: “There’s no doubt racing gives me what I need. I couldn’t envisage collecting stamps or doing history research. It is exhilarating and thrilling to feel that you are right on the edge but still in control.

“It’s the same as being an entrepreneur. We sometimes make the wrong decisions in business but we like to think that most of the time we make the right ones.

“Driving is very much like that. One error of judgement and it could all end in tears. Thankfully, while there have been plenty of times I have gone off the track, I have never had a serious accident. So I will keep pushing the envelope until I find where the breaking point is.”

6) The daredevil claiming motivation is key to everything

Much like Branson, Albert Bosch believes adventurer and entrepreneur are two titles that go hand in hand. He certainly knows what he’s talking about. After creating INVERGROUP in 2004, a platform for managing environmental and renewable energy projects, he single-handedly crossed the Antarctic, was the first driver to compete with a 100 per cent electric car, is a fan of the Dakar Rally and has climbed the highest mountains on each continent.

And all these adventures, in a way, taught him some valuable lessons. He claimed: “An adventure has a goal such as climbing Everest or reaching the South Pole, but it must fulfil an aim that involves the question why you do it and what for.

“They are not the same thing. To be motivated in anything, you need a purpose that gives you a reason and connects you with what you really want to be, with what you want to focus your effort and talent on. Goals will then emerge from this.”

You can find more about what he learned about human behavior in his adventures in the below video.