The idea of the Shipwreck Rally was born one sleepless night in early April, 2013. I had just been laid-off from a job I actually enjoyed for the first time in years. I had managed to transition from a web designer, spending countless hours re-arranging pixels and code in front of a lifeless monitor to shooting and editing video (for the same fashion company). I enjoyed it immensely, especially editing what I got to shoot. Not making enough money, the company got sold to private equity, and the incoming bosses downsized, re-structured, and built plenty of synergy. Within a couple of months, and in-between single sporadic layoffs, a random morning was chosen for 21 conveyor-belt goodbyes. I was the second to go that day, in one of two temporary offices, where contracted lawyers did their best to show a modicum of humanity and over-sell your severance package. No hard feelings of course ­- business is business, and in America, the cost will always come back to bite. Shortly after, I was hired back as an independent contractor, shooting and editing video as usual, since now there was nobody to do it.

After working simultaneously three jobs in college (one of which was full-time), and spending seven years afterwards in New York City working at various companies, always in front of a computer, the itch to do something different, something that mattered became stronger. Sagmeister’s rule about taking a sabbatical every seven years to recharge your batteries started sounding more rational by the minute. My best friend from high school tried to get me to do the Mongol Rally with him, an endurance trip for charity from London to Ulanbataar, Mongolia. Every year something always came up, and in reality, it was somewhat of an expensive proposition (for an American at least) and so we never got to go.

That one night back in April, racking my brain about what I could do – what I should do – with the two months of severance I had, and what would happen afterwards, when the money ran out, I decided to start my own damn ‘rally’. It would begin in New York and end in… no clue. I wanted it to be longer and harder than the Mongol, a test of fate and luck, of courage and rationed madness. You would ride your car or motorcycle and raise money for charity: travel and make a change. I clicked my phone open, scrolled to the bottom on a world map and found the southernmost city in South America: Ushuaia. It was right by Cape Horn, which marked the northern boundary of the Drake Passage: a hazardous place on this planet, with large waves and icebergs, strong winds and deadly currents. It became known as a treacherous place to sail through – a sailor’s graveyard – and home to many shipwrecks. Good thing I would be driving.

And so the Shipwreck Rally was born. Looking back, the layoff was really a blessing, allowing me the time to fully work out the idea – so I would like to take a moment and thank private equity. I started designing the logos, worked on the website, trademarked everything, hired lawyers, an illustrator, wrote privacy notices, filed as an LLC, researched and partnered with charities, and so much more, that it would be mentally painful to remind myself of it all over again. I got another job and started working full-time as a digital designer, while still shooting and editing videos as a freelancer. For months, I would come back from the office around 8PM and spend another 4-5 hours each night working on either videos or Shipwreck, or both, averaging 70-80 hours a week.

When I was finally able to open up the registration (aka charge money legally), it was already late summer, with only two months before the deadline, and the thought that nobody would find out or sign up finally dawned on me. I used whatever money I had left, on meager banner ads with Facebook and Google. Of course, nothing really happened: “I know I’m wasting half of my money on these ads, I just don’t know which half.”. I started taking online classes in ad-building-revenue-creating social media mumbo-jumbo and soon I wanted to shoot myself in the head, so I started learning Spanish instead.

The deadline came and I still had no sign-ups. This was now becoming a solo expedition. I asked my friends to join, giving the fact that most of the trip is already paid for, as my best selling point. The responses ranged from “You’re crazy” to “You’re going to die”. With this kind of feedback, I knew I was onto something. The idea of doing this alone, and seeing what happens became more and more attractive.

In addition, I was not finding a car. One of the rules of Shipwreck is that your car needs to have an engine smaller than 2 liters. I already had a car, a ’05 Volvo, but it was a 2.4, so I put it up for sale, and went to car places, hoping to maybe buy a cheap Civic and get some money back. No dice. If I didn’t want to upgrade to a nicer car, they weren’t going to sell me squat. So by the end, Bertha was going on this rally, whether I wanted to or not. I took her to a great mechanic (Minh’s Auto) in Brooklyn, changed some belts, and had an overall checkup. Good condition. Since I was now the only one doing the rally, I figured I could bend the engine rule a little. Bertha would be my teammate.

I started buying supplies and looking for people online that had done this kind of trips before, or remotely close. One person, Nicolas Rapp, stood out among the rest. Much like myself, Nicolas, a graphic designer, had grown tired of the office life in NYC, broke up with his girlfriend, quit his apartment, bought a Land Cruiser and circled the globe over the course of 15 months. He worked a few blocks from my office in midtown and so for a couple of months we met for lunch weekly, grabbing as much great advice as possible. ‘You’re scared of Central America? You should try driving through Iran with American plates’. And so, I’m immensely grateful to Nicolas and his help and his advice. You can check out his trip, Trans-World Expedition here.

On this note, I should probably end this post by first thanking my mother, who although stopped talking to me for a few weeks when she found out about Shipwreck, has now become my greatest supporter. Also, many thanks to the people who helped one way or another, whether it’s with the LLC (Meredith, Kim, Tara), by hosting me (Ioana, Huntley, Chelsea), giving money to the charities: Save the Children and Rainforest Foundation (Neil, Julia, Diana, Stefano, Thalita, Huntley, Paul, Praveen, Kim, Dan & Yoon, Melissa, Melissa K, Kenny, Josh, Rachel, Jane from Custom Ink) and those who always gave good advice and lent an ear when I needed it (Tom, Nora, Huntley, Cory, Luis, Myriam). Thank you all. I will try to post as much as I can, but time seems to fly by. I’m already two hours late crossing the border this morning, I still need to go to Staples and photocopy all my documents, an elderly gentleman in a suit has already asked me if I work with computers, because he has a few questions for me, if I don’t mind. So I need to go help him as soon as I finish my La Quinta breakfast sausages and Texas-shaped waffle.

Vroom, Vroom, Ahoyy!

These are the personal views and thoughts of the author and in no way shape or form reflect the views of Shipwreck Rally, LLC.