Updated: 10/23/2019 | October 23rd, 2019
I first met Lee a couple of years ago when he stumbled on my blog, bought my blogging course, and fired off crazy emails to me. Since then, we’ve become friends (he is the guy taking the selfie when my United flight had to make an emergency landing). Today, I want to share his story as Lee is the youngest American to visit every country in the world — and he has had his fair share of adventures along the way!
How did you get into traveling? You worked in finance before, right?
Yes, I worked in finance out of college for eight years. My objective was to make a lot of money on Wall Street, but a funny thing happened along the way. I studied abroad my junior year in college. This was the first time I ever left the United States. I went to London, and it completely changed my life. It was easily the best decision I ever made. It changed my view on the world and on my life goals in general.
So with that experience in my back pocket, I always knew I wanted to travel more. But like everyone, I needed to make money to fund the travel I wanted, so I got a proper Wall Street job, worked really hard, and did pretty well. Wall Street was a means to an end.
So, working in travel wasn’t always your goal?
Right. Aside from making money in finance and other businesses I am/was involved with, the goal was just to travel for fun and enjoy my life to the fullest. Working in travel just sort of happened.
I had written a few stories over the years for various travel websites just for fun. I started my blog back in 2006 to basically keep friends and family updated on what I was up to. Without ever thinking I would do travel-related things full-time, it just kind of evolved as I started doing more and more things in different facets of business, travel, and media.
How did you go about leaving Wall Street for travel?
Back in the summer of 2008, I simply resigned my position at a major Wall Street firm. Ironically, it happened right before the major collapse of several major firms, so it made me look smart, but it was pure coincidence.
Your “claim to fame” is that you are the youngest American to travel to every country. Was that the original goal or at some point were you like, “Hey, I’ve been to 100. What’s a 100 more!”
During my time abroad in college, I traveled to 15 countries in Europe. During school breaks and immediately after graduation, I took three other long backpacking trips around Asia, the Middle East, and Europe again. At that point, I realized I had visited some 50 countries. Knowing I would be working a ton, my goal was to visit 100 countries by the time I was 30. For whatever reason, I thought that sounded cool. I ended up achieving that goal at about 25.
Back in 2006, I got an email from a friend that there was actually a record of the youngest to visit every country in the world. I basically assessed how long I had to beat the record and where I had to go, and figured I’d give it a go. Even if I didn’t get the record, it’d still be fun and I’d get to see the whole world. Turns out it was a great decision, and I have done so much around the world.
What made you decide to pursue this goal? Did you leave your job to do it?
To be honest, the challenge of actually doing it made me decide to pursue the goal. It is not easy, obviously, but at that point in my life and in travel, I figured it was now or never, because I was more than halfway there already. I am also very competitive and goal-oriented. Not to mention, I thought it was pretty cool!
I didn’t specifically leave my job to pursue the goal. I left the job because I had had it with corporate life at that time in my life, and I needed a break after eight years.
Did you hit that record? At what age did you get to every country in the world?
Yes, I became the youngest American to visit every country in 2011 when I was 32 after safely visiting Libya. Technically, because of the addition of South Sudan as a sovereign nation, I am the youngest person to visit every country in the world. However, it is a bit of a grey area, and there is a lot of bureaucracy and red tape that goes into that title claim with the world-record powers that be, so for now, I go with the “youngest American” title, which I think is still pretty cool!
Depending on where you look, there are 25-50 people alive and 90 people total known or believed to have been to every country. I know just about all of them.
Do you ever picture yourself settling down?
I think I am settled down — although some people will have another definition of settled down. I own a great apartment in New York City, have great friends and family, and really am pretty happy. I can basically do whatever I want and work from anywhere. Every day is exciting because I never know what will happen.
I love waking up every morning, checking my emails, and seeing what’s on the agenda for the day, week, month, etc. I look at it like I’m playing with house money because this was never my intention.
You were in Libya when they were overthrowing Gaddafi. Tell us about that!
Libya was the last country I needed to visit to complete visiting every country in the world. I was originally supposed to go during March 2011, but the revolution had started and there was a no-fly zone, so I had no chance of getting in. So as the rebels took over as the Arab Spring continued, I kept an eye on things. I got word that eastern Libya was completely controlled by the rebels and that the remote eastern border with Egypt was open — sort of.
I also heard that since there was no government in place that they had dropped the visa restrictions and that it may be possible to get in through that border. So without really thinking about it, I flew to Cairo and then on to a small coastal town called Mersa Mutra, which is about 250 miles from the Libyan border.
I had no idea what I was going to do from Mersa Mutra. On the plane I noticed an educated-looking man wearing a suit and a rebel flag lapel pin. I asked if he spoke English and when he did I asked if he could help me translate to arrange a taxi or car to the border; I was willing to pay whatever it took.
It turned out this man was a Libyan dissident who was returning to Libya for the first time in 40 years. He also happened to work for the United Nations and had a UN passport. He told me that he would give me a ride all the way to Tubruk, Libya, in his brother’s minivan and obviously help me through the border process. I couldn’t believe what I was hearing and was obviously grateful.
Not only did he do just that but he also gave me a place to stay in Tubruk, dinner with his family — whom he had not seen in 40 years — and transportation with his friend all the way back to Cairo — which is a 12-hour drive — a few days later. He refused to take a dime. It was unbelievable how nice their family was to me, and I am forever indebted.
There was also a small matter of getting caught at the border in a firefight between some Chinese smugglers and the Libyan rebels. We all had to duck and fire the car in reverse in order to not get shot. That was pretty scary, and after three hours we made it through!
What travel advice would you give to someone who has never traveled before?
My advice to someone who has never traveled before would be to go to Europe. Buy a Eurail pass and hit the major cities. Get to feel comfortable and see how cool it is to experience a different country, language, food, culture, etc., each time you make a move — all so close together. That should whet their appetite to travel to less-developed nations.
Also, the well-trodden routes of Southeast Asia and Australia work too, but I think the history of Europe will hit home a little harder, as they’ll get more than just partying on the backpacker circuit.
You’re a sports guy. Where was your most memorable sports experience in the world?
Sports are my passion. Playing or watching; it doesn’t matter — I like them all. I am fortunate to have been to just about every major sporting event in the world, like the Superbowl, Olympics, Champions league, World Cup, Rugby World Cup, etc. I plan a lot of my trips around sporting events. It’s difficult to pick just one, but I will say the 2001 World Series.
This was the World Series between the New York Yankees and Arizona Diamondbacks that took place six weeks after September 11th. I am a die-hard, lifelong Yankees fan, a New Yorker, and I also worked in the World Trade Center, so emotions ran very high. The middle three games of that series at Yankee Stadium in the Bronx were amazing, exciting, and emotional. The Yankees won all three games in a dramatic late-inning fashion. They went on to lose the series in seven games, but that didn’t matter. Being a part of that series in New York is something I will never forget.
Traveling so much as an American, did your friends have a hard time understanding your lifestyle?
I am fortunate to have very good groups of friends, many of whom love to travel and have traveled a lot with me. The ones that don’t travel just know it’s a part of me and love reading my stories on my site, but it’s even better hearing the unedited, no-holds-barred stories in person! I always make time for my friends. I go visit them wherever they live, welcome them to New York anytime, and I never miss big events.
If you lose sight of your friends and family, what will you have left?
Book Your Trip: Logistical Tips and Tricks
Book Your Flight
Find a cheap flight by using Skyscanner or Momondo. They are my two favorite search engines because they search websites and airlines around the globe so you always know no stone is left unturned.
Book Your Accommodation
You can book your hostel with Hostelworld as they have the largest inventory. If you want to stay somewhere other than a hostel, use Booking.com as they consistently return the cheapest rates for guesthouses and cheap hotels. I use them all the time.
Don’t Forget Travel Insurance
Travel insurance will protect you against illness, injury, theft, and cancellations. It’s comprehensive protection in case anything goes wrong. I never go on a trip without it as I’ve had to use it many times in the past. I’ve been using World Nomads for ten years. My favorite companies that offer the best service and value are:
Looking for the best companies to save money with?
Check out my resource page for the best companies to use when you travel! I list all the ones I use to save money when I travel – and that will save you time and money too!