30 countries and counting with Gabe Krebs


A finance major who learned the value in investing in himself early on, Gabe Krebs has traveled to over 30 countries since graduating college. We caught up with him for this Risk Takers interview to discuss travel hacks, entrepreneurship, and some of the downsides to his lifestyle on the road.

How did you begin working for yourself and has entrepreneurship enabled you to travel?

For whatever reason I’ve always had the entrepreneurship itch. When I was 14 I started my first real business by drop shipping on eBay and I quickly became a PowerSeller by logging in between study hall and football practice. Things couldn’t have been better; that is until taxes were due. PayPal ran my social security number and realized I didn’t meet their minimum age requirement of 18. I was banned for life, and I was crushed. Well, that is until my father let me open a new account under his name. Back in business. I have tried a lot of side projects over the years — some successful, some not. It wasn’t until shortly after I graduated from university that one of my companies gained some traction. My partner and I ended up taking on investment from a private equity firm based in Paris, France to expand internationally. Doing business in northern Europe enabled me to easily see much of mainland Europe. In my experience, the work for an entrepreneur comes in waves. Some weeks it feels like there isn’t enough coffee in North America to accomplish the amount of work that is in queue, while other weeks can be flexible enough to take a trip. Taking advantage of the weeks where I could either take off or work remotely has certainly enabled me to travel more than the average person.

What’s the wildest thing you’ve done for money to support your travels?

I have not (yet) done anything noteworthy for money, but I am a huge mile enthusiast or as others refer to it, a travel hacker. In other words, I’ve done an endless list of unorthodox things for miles and points to help fund my travels. The first story that comes to mind is when Hilton was running a promotion targeted towards Australians. I thought it would be entertaining to give my best attempt at an Aussie accent when I called in. It took about two words after I said “G’day mate” for me to remember my Australian accent was nonexistent. Not even thirty seconds into the call my voice nervously cracked mid sentence. I gave up on the impersonation and awkwardly continued to speak in my (then much defeated) normal voice. To my luck the representative was either so confused or felt so sorry for me, she gave me the free night certificate.

How the heck does one afford to travel as much as you do?

I normally have one simple answer for this question: I prioritize travel. But to give a more practical answer, any time I am out of town, I rent out my apartment on Airbnb. I’m lucky enough to live in a popular area where the money I receive from renting almost always more than offsets my traveling costs. Regardless, even if you are able to subsidize half of your trip, it makes justifying traveling so much easier.

Have you ever broken the law while traveling?

Whenever I’m crossed with legal morality questions abroad, I think back to when I was debating driving in a foreign country for the first time. I was in Athens, Greece and it made much more sense for my travel plans to have a car. I asked a local what the potential penalties would be for driving without an international driver’s license and he looked at me and said “it’s only breaking the law if you get caught”. I liked this answer, and decided to proceed with renting a car. This certainly ignited the rebel side within me and made traveling more fun. As most of us do when making a decision that goes against the rules, I calculate the potential consequences compared to the likelihood of getting caught and somehow trust my intuition of what lies within and outside of my comfort zone. A very anticlimactic story about breaking the law is in 2014 when I was headed to Singapore and my friend reminded me that chewing gum was against the law. Well, the one item I purchased at the airport before taking off was one a pack of Trident. I kept my cool and smuggled the pack past customs like a boss, tucked away in my secret pocket on my backpack. I was curious to see what would happen if I got caught, so anytime I would pass a police officer I would dramatically chew a piece, trying to get their attention, to no avail.

I was offered drugs multiple times on beaches in Thailand and I would, quite literally, run the opposite direction because drug penalties can be very extreme throughout most of SE Asia. Conversely, I’ve been able to experience some guided spiritual experiences that technically were illegal, but widely accepted among South American countries. Every time I travel I make it a point to become well acquainted with the local laws to make a well informed decision. But at the end of the day I always trust my gut.


What inspires you to keep travelling, do you ever get discouraged?

The more I travel the more encouragement I receive from those who are older and much wiser than I am. I constantly hear variations of “It’s fantastic that you’re traveling now, I wish I would have done that!” The sound of regret in their voice makes me cringe every time I hear it, and it’s reassuring to have the support of individuals who have lived a lot more life than I have.

To answer the second part of the question, at times this lifestyle can be discouraging. It boils down to one thing: Opportunity cost. For most millennials it will never get easier than this to travel, on the same token your twenties can be well spent building a financial and career foundation. Personally, I have a constant internal negotiation on how I allocate my income. As a finance major, I understand the concept of compounding interest as well as anyone. However, I’m also a firm believer in investing into yourself. The more we experience, the more we have to offer others. The experiences I’ve had over the past five years will undoubtedly pay greater dividends over my lifetime than any financial investment I could have made.

Do you consider yourself a risk taker/daredevil and why?

Absolutely.. more risk more reward, right? I can’t imagine a life without risk. I’ve maxed out credit cards to start businesses, slept on strangers couches, trusted sketchy street vendors with my passport to expedite a visa, been upgraded to first class by politely asking, spent every last dollar to my name while abroad, bought friends plane tickets without asking them, jumped out of airplanes, and flown to a different country just to ask a girl on a date. Sometimes it works out, others, well not so much, but the motto is “it is always worth it.” Most of the great things that I’ve experienced in life have happened because I decided to take a risk.

What’s the downside to your lifestyle?

The past year I’ve been away more than I have been home. When you’re out of town that often, it is inevitable that you are going to miss birthdays, holidays, reunions, etc. I do my best to get creative and let people back home know I’m thinking of them, but nothing is more special than quality facetime together (and no I’m not talking about the iPhone app). Long term solo travel can also be very testing. There’s no one to fall back on, and most days are starting at ground zero to make new friends. It’s exciting and I wouldn’t want to change my lifestyle, but people need to keep in mind it’s not all fun times like Instagram can easily portray. During solo travel you learn to be at ease with being bored, which is actually a topic I am currently writing about! Future blog post forthcoming.


How do you decide your next destination?

I have a large wall sized map in my room, and after each trip I head home, put on a blindfold, and throw a dart until I strike land. And that would be the coolest fact about me if it were true; sadly it’s not. However, that doesn’t mean I’m not spontaneous in a lot of my travel plans. I follow various travel blogs and try and hop on mistake fares any chance I have. For example, next week I am headed to New Delhi because I found a $200 round trip flight from San Francisco that I couldn’t afford not to take.

Biggest advice to young folks on how to make travel a reality?

If you want to travel, you must make it a priority. I’ve been to 35+ countries, but I drive a car that is older than I am. When I am home I’ll occasionally go out with my friends and I’m astonished at how casual it is to spend close to $100 in a single weekend between dinner, drinks, and a recovery brunch. That’s $400 a month that could be put into a travel fund. It wouldn’t take very long to fund a trip, especially if the flight can be paid for in miles! Which leads me to my next point, researching methods on how to accumulate miles is well worth the investment. Flights normally account for the largest portion of the budget, but there are many ways to significantly lower the cost. Once at a destination the remaining costs can be comparable, if not cheaper, than living in your hometown, depending on your travel style. Of course this doesn’t always hold true, but generally it does.


gabeGabe — a product of the Pacific Northwest — prefers nothing more than a day well spent outdoors. After experiencing his first taste of traveling abroad by studying on a cruise ship, Gabe never stopped seeking any excuse to keep traveling after the voyage ended. Gabe currently spends roughly half of his time in Portland, Oregon, and the other half traveling while he works remotely. Earlier this year, Gabe reached his 30th country, and isn’t looking to slow down anytime soon!

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