Extreme sports, bike-a-thons and winter Olympics – How far do entrepreneurs and investors go for a thrill?

extreme entrepreneur
extreme entrepreneur

Some leave the office to go on vacation or relax with a good book. Others take off to kiteboard, prepare for competition in the upcoming winter Olympics or gear up for a hardcore bike-a-thon. Writer and journalist Matthew Carter takes a closer look at the extreme routes some startup founders and VCs take to get an adrenalin fix…


Entrepreneurs may take a break from the office to vacation, relax, or investigate the next promising startup opportunity. But for serial entrepreneur and i/o Ventures‘ cofounder Paul Bragiel, taking a hiatus means swapping citizenships and competing for medals.

A contender for the cross-country skiing competition in the upcoming Sochi 2014 Winter Olympics, Bragiel (below) is not vying to compete for his native USA. In fact, the US cross-country team is one of the most sought-after in the world, with only a few slots allotted to capable competitors. So Bragiel is looking elsewhere to a blaze a new trail under an entirely different passport.

width="131"Until now, it remained uncertain as to what other country would give the advantageous 35-year-old the go-ahead to compete. But on the topic of his new citizenship, he remains tight-lipped. “I don’t want to jinx anything and say anything publicly yet,” he says. “But I had the president of the country approve it personally, so I think I’m in good hands.”

Bragiel’s background in founding tech seed funds in foreign countries has helped with the legwork for negotiations to compete – experiences you can’t gain in the boardroom. “Most governments and politicians in the world are used to people kissing their arses. In other words, a ton of yes-men,” he jokes. “I try to usually politely tell them where they are performing poorly. A lot of it is also being able to relate and break things down that will fit within their respective agendas.”

If the regions where Bragiel has started the funds are any indication of his surrogate country, we could see him competing for anywhere in sub-Saharan Africa to Southeast Asia.

Sporting and startups

Bragiel’s desire for athletics is nothing new for a successful VC of his ilk but what does this mean for i/o Ventures – and their mentorship of promising startups? “They know I’m a bit of an adventure-seeker and that I occasionally go on personal quests like this,” he explains. “We worked out a schedule that compensates for my absence and I’m still super involved with all of our current companies over email.” Even so, staying on top of it can be difficult when your emails are being sent from the glacier on which you’re training.


Making such a sacrifice in the name of competitive athletics is a rarity in this field, but some VCs have had altruistic results in their pursuit of sport. Angle Technology’s director Jothy Rosenberg is currently gearing up for a 192-mile pan-Massachusetts bike-a-thon that will see 100 per cent of the fundraising donated to the Dana-Farber Cancer Institute. Moreover, Rosenberg is doing the challenge without the use of his right leg; it was amputated at 16 when he was diagnosed with osteosarcoma.

Bragiel isn’t faced with the same adversity as Rosenberg but has had to find sponsorship to train. “Most of these [ski] brands tend to see elite athletes and we’re coming to them with a human-interest story angle,” he says. And just like one of the many startups Bragiel has had experience with, it’s now up to him to show evidence of funding potential.

“I’m a total outsider in this world and the underdog; also you need to build a team. Feels exactly like a startup in that sense,” Braigel affirmed. “Only major difference is that instead of building a product, the product is me.”

Some entrepreneurs have been able to build a product and be physically active at the same time. Take for example “People Search” mogul Nick Matzorkis who founded Sup ATX, which popularised the sport of stand-up paddling. If you’re lucky enough to have an invitation to a MaiTai event, you will have a chance to pitch your startup idea to Sir Richard Branson while you learn how to kiteboard on a private island.

Jet ski

“Don’t start when you’re 35”

Bragiel holds high the hope of long-lasting recognition and not just fine-tuning a hobby. This is also the case for MeLLmo software developer Jerry Jones, who is one of the top ten freeride jet skiers in the world – or borrowing community NeighborGoods founder Micki Krimmel, who plays for a roller derby team currently ranked #7 in the world.

Yet if Bragiel is to sell his dedication as a fully adorned Olympian, he has quite the route to go before he can intimidate his competition. “It’s a very different world. Athletes have to be very in-tune with their bodies, to a point that I never understood before,” he explained. “My body hates me everyday… I’ve heard from many Olympians that besides the super elite ones that get big sponsors, most end up 50 to 100k in debt after making a run at the Olympics. Now that is dedication!”

And if you’re a tech entrepreneur looking to make the jump into the world of organised sports, what’s Bragiel’s main point of advice for you? “Don’t start when you’re 35.”

Paul Bragiel’s first qualifying race will take place on 27 July in Falls Creek, Australia.

Image credits:
featured image – flickr user bikephotomusic
Paul Bragiel – flickr user miss_rogue
cross country skiing – flickr user Jon Kristian Bernhardsen
jet ski – flickr user bigtallguy

For related posts, check out:

Unplugging, “digital detoxes” and Offtime – How do you maintain an online/offline balance in a hyperconnected world?
Will you really be proud of having your inbox at zero? 10 tips for entrepreneurs to put the “life” back into their work-life balance
Love, muesli and Nigeria – how the internet changed everything