There were many times during Chris Guillebeau’s epic quest to visit every country on the planet — 193, by the UN’s count — that he didn’t think he’d make it. His vehicle went MIA on a beach in Spain. He was detained by the cops in Eritrea. His passport was confiscated in Saudi Arabia. And in Comoros, a tiny island nation off the coast of Mozambique, he just flat-out ran out of money.

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But none of that derailed him. Though Guillebeau was just 28 when he made his resolution, imposing a deadline of age 35, he didn’t let his relative youth or the obstacles he encountered dissuade him. “Some things sucked at the moment, but I knew I couldn’t quit when I was at 120, 130, 150 countries,” he says. “I didn’t want to be the guy who almost went to every country in the world.”

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Guillebeau came up with his plan for world domination (kind of) while he was traveling in Eastern Europe after a four-year tour of duty in West Africa, where he had been volunteering for the medical charity Mercy Ships. After writing out a list of all the countries he’d visited by that point, he had an incredible inventory — for most people, anyway — of more than 50 nations. But for this traveler, entrepreneur, and author, it wasn’t enough.

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“It wasn’t some strategic plan,” Guillebeau says, reflecting on his decision to turn 50 into 100 into All The Countries. “It was just this crazy idea. Then I built an environment around it and I thought I’d just see if I could make it happen.”

Now a resident of Portland, Oregon, Guillebeau credits his youth with preparing him for a life on the road. When he was a kid, his mom married a military man who always had their family on the move. They lived in the Philippines for a few years and stopped for a while in Montana, but never remained in one place for long. “It wasn’t the greatest childhood in some ways, but it helped with what I do now, in that I was comfortable just being in many different places,” he says.

Guillebeau’s desire to travel isn’t just a casual sightseeing impulse, either. In 2002, in search of a meaningful “post-9/11” volunteer experience, he started working for Mercy Ships in Sierra Leone. Until 2006, he worked on one of the org’s hospital ships off the West African coast — hardly a lazy beach vacation.

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“After my time volunteering in West Africa I’d go to other places and just be like, ‘Oh man, this is so much easier,” because you don’t have to “deal with geopolitical things,” he says. “It’s like if you’re in New York and need to fly to Chicago but you have to go to the West Coast first just to get back to Chicago. After doing that for a few years, going most other places seemed easy.”

Of course, though Guillebeau ended up putting a pin in every country on the global map in under a decade, it wasn’t always smooth sailing. Any mass amount of travel such as what Guillebeau undertook is going to meet with some rough seas. One of his favorite stories concerns how he talked his way into Pakistan. When it came time for him to make his way into that country, Guillebeau hadn’t yet been granted a visitor’s visa. But he went anyway.

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He was in Hong Kong, where the flight to Pakistan was leaving from, and decided to print out any and all relevant paperwork. “From working in West Africa, I learned that countries are always looking for paperwork, even if you don’t have the exact right [forms],” he says. “So I just decided to bring everything. I brought the visa application that didn’t go through, I printed out my website, everything.”

His hail-mary strategy worked. He bluffed his way onto the flight and then got stuck in a room at the airport after landing. No one was providing him with any information — but, in the end, he was allowed entry because, according to Guillebeau, they just didn’t really have anywhere else to send him. He ended up spending a week in Pakistan and even met some readers of his blog.

Saudi Arabia was even more harrowing. Upon arrival, Guillebeau was detained and his passport confiscated. (The fact that he was traveling for fun and not business had spooked the Saudi border guards.) Eventually they let him go to his hotel, but every few hours someone came by to check on his whereabouts. After three days of this, Chris decided it was time to quit Riyadh. Thankfully, his passport was awaiting him at the airport. “I was not invited to return,” he says.

Eventually, though, Guillebeau completed the crazy goal he’d set for himself. It was an emotional time for him. He thought, “What do I do now?” He decided he needed to find a new focus, in part by “extrapolating meaning” from having visited literally the entire world. That effort led directly to his first book, The Happiness of Pursuit. “It’s about my journey and other people’s journeys that I’ve heard about during mine,” he says. “It’s about our quests.”

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Which brings Guillebeau to what he is doing now. “It’s all about community,” he says. At the beginning of his travels, Guillebeau, a self-professed introvert, would easily go 10 days on his own. He says he never had the need to travel with friends or meet up with a bunch of people at a hostel. But, the most rewarding parts of his travel became connecting with others.

“The best part of the journey is sharing your experiences,” he says. “All these great people came out of the woodwork and it was so amazing to hear their stories. My whole thing shifted from just ‘a guy on a mission’ to now being fortunate enough to curate or collect all these great stories people have about doing great stuff.”

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Ultimately, that’s what Guillebeau wants the rest of his life’s work to be. “I want to share these stories and just bring people together.”

The next iteration of this desire comes not from travel, but from the startup world. Guillebeau has a serious and longstanding need not to “work for the man,” and so he is very invested in encouraging independent businesses and people doing freelance work — the opposite approach of Silicon Valley–type startups, which are far more organization-driven.

Guillebeau realized early on that, while he didn’t want to be in an office all day, he still liked working hard and being a part of creative projects. Among other gigs, he worked in online advertising and consulting, which were key parts of his journey to being where he wants to be and doing what he wants to do. “I want people to know they can make a decent living this way and they can also do whatever it is they want to do,” he says.

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In this community of free-spirited yet fiercely driven people, Guillebeau is a kind of amateur oral historian, collecting stories about how these individuals made their own way in the world and built something for themselves. “There’s been books about startups, but no one had really talked to these independent entrepreneurs before,” he says. “I wanted to give them a voice.”

Luke McCormick is a writer living in Brooklyn. He has written for SPIN, rollingstone.com and other publications.

This post is a sponsored collaboration between Wild Turkey and Studio@Gawker.