What Crossing the Arctic Ocean Taught This VC about Entrepreneurship

Four lessons from an incredible adventure to remember
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New frontiers have become harder to find than the adventurers who used to seek them. But that doesn’t mean they aren’t still out there.

As a venture capitalist, I regularly take a lesson from a crazy trip I took with three highly-skilled teammates in a rowboat across the Arctic Ocean. It almost killed us, and landed us in the Guinness Book of World Records. But more than anything else, it has many parallels to the entrepreneurs who set out on the adventure of starting a company.

Why the Arctic? We wanted to do something big. Something different. Something that hadn’t been done before. But we also wanted to make an impact. In this case, we wanted to draw attention to the melting Arctic ice. So we decided we would be the first people to cross that frigid body of water -- in a rowboat.

So, on Aug. 28, 2012, we launched from the northernmost continually inhabited town in the world -- Inuvik, Canada -- in a bid to become the first team ever to complete an unsupported, non-stop, record-setting voyage across the Arctic Ocean.

I was interviewed about the expedition in the video you see above.

Related: Why You Must Embrace the Danger of Adventure to Lead Effectively

My teammates -- Paul Ridley, Scott Mortensen and Neal Mueller -- and I would spend 41 days in that 29-foot-long rowboat. It sat six feet across at its widest, and the four of us were never farther away than eight feet from one another the entire journey. We rowed four hours on, four hours off, for 24 hours a day, through what turned out to be one of the largest storm seasons in Arctic history.

We endured a lot of trials -- not unlike those suffered by most startups. Our water maker broke while we were five days away from any human. We cobbled together a workaround, but we still had to ration our water, and by extension our dehydrated food, for the rest of the trip.

We also stumbled through what we later found out was the 13th largest storm in Arctic history -- a hurricane with large, breaking waves that hammered our rowboat as we made our way along the Northern Passage.

There’s no doubt it was dangerous. There were more than a few times we thought it was never going to work, and that we might actually die. Two of our team members had climbed Mt. Everest, and they insisted this Arctic trek was the most dangerous thing they’d ever done. At the time, it was rough.

Related: How a Near-Death Mountain Climb Launched One of the Adventure World's Best-Known Brands

But we didn’t know what we didn’t know. And that’s a lot like starting a business. You don’t know what you don’t know until you’ve already committed. But with luck, like us, you make it through.

And, now, looking back, it was moments like those that made everything so exciting -- and so worthwhile. Now, instead of it being a terrifying flashback, it’s a fun story to tell.

I still think about how much that journey resembles a lot of startups. Here are the lessons I take away from that trip for entrepreneurs

1. Build a team that you want to be there through the worst of times.

We had to build a team and work incredibly close to (and with) one another for long hours. Stuck in that crowded boat, with miles of freezing water behind us and weeks of thirsty rowing ahead of us, it didn’t feel very good at the time.

2. Raise enough of the right kind of resources.

We had to raise money for the venture. It took time, but with a couple of large sponsors and dozens of smaller ones, we raised more than $250,000 for the expedition, including sponsorships to cover our gear. There are times when getting someone to believe in you -- and your vision -- can be just as difficult as any six-week voyage.

3. Get ready to work harder than you have before.

It’s often a good thing that we don’t know what we don’t know. You have to go out there and accomplish something no one has ever done before. It doesn’t matter if you’re crossing a hazardous body of water or putting your brand on display for public judgment; either one can feel like life or death.

Related: What Running with the Bulls and Polar Exploration Can Teach Entrepreneurs (Podcast)

4. Work through your fears of failure

Our team worried about "what if we don't succeed." Of course in this case it was also "what if we don't survive?" Founders face huge uncertainties while building a company. The trick is to acknowledge those fears as a team and if you’re going to fall, fall forward.

There were so many things we wanted to do at the time that still feel like failures. For example, we’d agreed to run some research and collect data, but once we were in the water we spent the entire trip in full-on survival mode. So, we failed that scientist.

But that’s what entrepreneurs do. We are eternally optimistic and overcommit. And some things don’t work out. But even then, those little failures are as instructive as the overall success.

Looking back on my Arctic journey now, as an investor, startups seem a lot less risky

I came back 40 pounds lighter, an expedition beard heavier and loaded with a world’s worth of perspective.

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