We’d given ourselves a year to pull it off and our time was up. Between the two of us we had $186 dollars. No car, no house, no dog, no job. And that’s what was so great. We had nothing to lose. We’d raised nearly a million dollars from people we’d never met for a boat that didn’t exist. But it wasn’t enough. We hadn’t met our goal. We had to give all the money back. The proverbial smoke but no cigar.

I looked across at Jody, poured her a glass of wine and we made a toast to one of the best years we’d ever lived. That fateful night came to be known as the Last Supper. It was the last week of October 2006 in Seattle, Washington.

Coincidentally, it was exactly one year prior to this night that we’d been walking on a beach in Thailand. We had a broken boat we couldn’t afford and 8 years of wandering the Pacific in our wake and all we knew was that we weren’t done. But we also didn’t know how we could continue. What we wanted seemed like an absurd proposition. To sail and explore the world totally on our own terms; with a modern luxury yacht with cool people we wanted to spend time with; and get them to foot the bill!

We hatched a plan but had no idea how to execute it so we just purposefully stumbled along. The first order of business was selling the boat we had. After paying off all the debts we banked $35,000. With that money we figured we could move back to the States, live for a year, develop a website, create the contracts, get sponsors, set up the business and live our dream.

Our dream looked like this on paper: Our company, Offshore Odysseys, would buy a big catamaran with other people’s money. These people would in turn own shares in the company, giving them access to the boat each year for a planned 5-year expedition to circumnavigate the globe. Our theme would be kitesurfing. Kitesurfers only need wind to have a good time, and I knew a great deal about where to find wind.

Rob Born, part boat owner, scores a kitesurfing session in the Cape Verde Islands off the coast of Africa.

Rob Born, part boat owner, scores a kitesurfing session in the Cape Verde Islands off the coast of Africa.

My dad always told me that two things motivate people. Fear of loss, and need for gain. So we used them both. While we were desperate to sell the shares we made it look like gaining access to the expedition would only be made available to people who could prove they were worthy, and that only a very limited number of shares were available (fear of loss). And then we appealed to a dream that many people share. To sail the world. Time on this earth is limited and if you don’t do it now, you won’t do it (need for gain).

By May we’d moved back to the States, the website was built, the contracts were ready and we were open for business. And not much happened. Every few weeks we’d sell a share, but we needed to sell a few every week to make our goal. We pressed on. We edited a video showing what people could expect, signed on sponsors, and spent a large chunk of our rapidly depleting funds on magazine ads. We worked insanely long hours and did a lot of headscratching but every aspect of what we were doing was entrepreneurial and creative and totally new which meant every day held a surprise. I remember trying to sell a share while hiding under a kite in 35-knot winds on the beach near Hood River, Oregon. The potential client said, “Well I’m pretty much ready to sign on, I just have one more question….what happens if you die?” I told him I’d have to get back to him on that one. But I never did, as I never figured it out. The truth was we’d be in a lot of trouble. But he bought the share.

And there we were, at the Last Supper. I looked over at Jody and confessed that we didn’t have enough money to live more than a few more days, that our year was up, that our dream was dead, that we needed to get real jobs. No disappointment registered in her eyes, and I know that none did in mine either. We’d had a stupidly good year albeit filled with mistakes and wrong turns but what story of success isn’t? I’d never sold a single thing in my life and we’d raised nearly a million dollars. No big deal for the guys on Wall Street, but a pretty big deal for us. To do it I learned I actually didn’t need to say anything when a potential client would call. Inevitably they would talk themselves into it. Selling dreams turns out to be pretty easy.

I emailed one of our investors who had become a close friend, and who was planning his retirement around the expedition. He asked me how many shares we needed to sell to make our goal. It wasn’t many so he just bought them. Six days later I was on a plane to Europe and signed the contracts to buy Discovery, a 57 foot catamaran priced at nearly $1.2 million dollars. A month later I returned to Europe and closed the deal on the 20th of December, a few scant hours before Europe pretty much shuts down for a month. Nine hours later armed with a Leatherman, a month’s worth of food, not a single spare, no tools, no bedding, a single pot in the galley, and two crewmembers who had never sailed offshore, we left Italy and sailed 4,600 miles across the Atlantic to begin The Best Odyssey.

I’ve told this story to a lot of people over the years but it still blows me away. I couldn’t believe it was happening at the time, and now that we completed it I sometimes wonder if it actually did.

Neither Jody nor I consider ourselves planners, but somehow we planned what is certainly one of the most complex expeditions that ever happened. If someone died, got hurt, or got ill the show had to carry on. No calling in sick, no taking a day off. At times I felt like I was living inside a pressure cooker that had no relief valve. More than once Jody and I had long, tearful, serious talks about pulling the plug. But always these times would pass and be replaced with some of the most precious and happiest moments I’ve ever lived. I’m humbly proud of what we’ve achieved and at the same time scared that what we’ve achieved is only human, which succumbs like everything…to history.

Emergency floor triage after Gavin breaks a rib, courtesy of his SUP.

Emergency floor triage after Gavin breaks a rib, courtesy of his SUP.

I think our success hinged on three things. One, we never did it for the money. That was actually never even part of the equation. In fact all those years of the Best Odyssey my salary always just went right back into the boat as we were forever underfunded. If our priority was money we would have quit the first year. Our motivation was always to see and share this precious earth with folks who brought their own unique gifts and passions to the expedition. Two, we appealed to the child in all of us. Children have a natural wanderlust to experience the world that is all around them. This curiosity is inevitably squeezed and diluted by the demands of the society in which we inhabit. Three, an unrelenting totally audacious work ethic. I think people who were not intimately familiar with the Best Odyssey imagined that Jody and I were firstly pretty well off. And secondly, that we were “living the dream.” The first I’ve already dispelled — we were broke when we started and we weren’t much better when it all ended. The second was true, we were living the dream but even now as I write this more than 2 years after we finished the Best Odyssey I know I haven’t recovered from the output that was required for the expedition to run its course. Those 5 years at sea filled my soul with moments too many and too precious to even catalog, but they also nearly broke me. The exhaustion, the stress, the pain that I went through to pull it off was something I thought would ease with time. It hasn’t. But would I do it all over again? Of course!

Guilty as sin. There’s a law against kiting in the Panama Canal and apparently, the canal cops take it seriously because they’re chasing down a rebellious Moises Niddam.

I believe to provide a truly unique and special experience you have to walk a very fine line on the risk spectrum. There’s a reason there are so many boats in the BVI’s and the Mediterranean. I’m not knocking those places, but that was never our gig. We promised adventure, real adventure, the kind that takes imagination and confidence to go places that very few ever have. We could never promise what was going to happen because we had no idea ourselves. And it meant things were going to go wrong, which was kind of a double-edged sword. When things went wrong it made my job infinitely harder, but it would have been awfully boring if everything went right.

When the Best Odyssey ended in October 2011 Jody and I got on a plane to India to paraglide for a few weeks and get as far away from the ocean as we could. We were finished; we’d completed what we set out to do. We’d never once spoken or even thought about what was next. We never considered that Offshore Odysseys was much more than a name, let alone a company or a brand. When we got back from India, Pete Cabrinha called out of the blue and asked what we were doing next. We had a boat that needed an awful lot of work before we could sell her, and the market for boats was dismal. The company had a ton of debt; we were wracking up a bill we couldn’t pay in a Spanish boat yard. Things looked pretty bleak and I didn’t have an answer. “Why don’t you guys do it again?” Pete questioned.

And just like that our whole perspective shifted. We’d built something without even realizing it. All the media, press, videos, articles and captain’s logs I’d written after all those trips gave us access to even more people with the dream of disappearing over the horizon.

The Best Odyssey taught us a few things so we tweaked the structure a bit, made it a membership program instead of selling ownership shares and simply made an announcement and a few changes to the website. No advertising, no hunting for sponsors, no scratching our heads. We sold out of memberships in a few short months. All the debts were retired. We got paid for all those years of work; we purchased Discovery outright so now we own the boat free and clear. Discovery sat on the hard for 10 months and received $200,000 of upgrades (most of them aimed to “green” our vessel to operate with a greatly reduced carbon footprint), all overseen by her new skipper, an Aussie named Seon Crockford. Like me he’s got salt water in his veins and in his eyes I see the same passion and wanderlust that drove me for all those years. The Cabrinha Quest was born.

These days my office is a long ways from the ocean. My window looks out on the White Cloud mountain range in Sun Valley, Idaho. It’s an inspiring view, one I’ve grown to love as much as all those endless horizons at sea. Jody and I run what we call the back end: The social media, the books, the sponsors and the members. I spend the rest of my days paragliding all around the world and go out to run Discovery from time to time to keep the skills honed and give the regular crew some time off. We’re currently designing another yacht to add to the Quest, an 80 foot environmentally responsible beauty that I suppose we’ll name “Discovery II”. As long as people keep dreaming, we’ll always have a business.

School teaches us that to be a successful entrepreneur or have a successful business you must identify a market need, real or perceived, and fill it. School doesn’t teach us to follow our passions. We are trained to fit in, to follow the rules. We asked ourselves what our dream was and did our best to live it. On our own terms. At times the stress of it was as suffocating as drowning, but to witness the smiles and hear what the expedition meant to those who joined was more reward than I could ever get from a paycheck. Even in the very dark times I knew my time on the boat was something I should never take for granted, and hopefully I never did.

Offshore Odysseys, operator of the Best Odyssey and the Cabrinha Quest is pleased to announce the launch of Cabrinha Quest II, a continuation of the acclaimed seafaring expedition which has taken its members to the most remote and dynamic kitesurfing and surfing locations around the world for the past 13 years. Like the preceding expeditions, the Cabrinha Quest II will be a five year circumnavigation commencing January 2019. Memberships applications are currently being accepted. For more information visit www.offshoreodysseys.com.

This story first appeared in The Kiteboarder Magazine’s Spring 2014 Issue: Volume 11, No. 1. Want more inspiring stories? Subscribe.