Ep. 209: Bobby Casey – Travel the World (Forever) and Never Feel Broke Again…


I heard an eight-year-old kid tell another eight-year-old that he’s not welcome in his home. He said “Trump or Clinton?”


And that was that. They kept walking. Kept debating and I bet nothing happened. I bet they’re still friends.

Some people are either all talk or afraid.

Or both.

I try not to be either. I try to listen, come up with ideas, and be grateful. Because if I listen, I learn. And then I can say two sweet words… “thank you.”

How many people said, “If Trump becomes president, I’m leaving the country.” Or the other way around?

There’s only one reason why I’d ever even consider packing. And Bobby Casey spelled it out for me.

“Americans don’t understand how insanely expensive it is to live in the U.S.,” Bobby said on my podcast.  He sold everything he owned and left the country in 2009. Right after the market crashed. Now he works all over the world. And helps people get off the grid.

I wanted to know how he did it.

And why…

“I hated my customers,” he said. “I hated my employees, I hated my job, I hated my business.”

“But what made you think you could sell all your belonging and travel the world forever?”

“Weren’t you scared you would run out of money?”

“I just knew I’d work it out,” he said. “I’d make some money.”

I couldn’t do it. It’s easy to be uncertain when you’re level of the unknown isn’t going to erupt your central nervous system.

But Bobby had motivation.

“My happiness and my quality of life is much more important than cashing out on a business,” he said. “I didn’t care. I wanted to be happy again.”

So he got rid of everything. He gave away motorcycles. (He had 27). Then he bought two one-way tickets to Prague. One for him. And one for his 9-year-old son.

“We’d never been there.”

The rest of his family moved a few weeks later. He has three kids.

“What about friends? And school?” I asked.

“My daughter, she’s 20, she’s a rapper in London. She did two years of virtual school. And she can make friends anywhere. It’s her personality type.” His other two kids enrolled locally.

I had 100 questions. “How’d you get the confidence? What type of freelance work did you do?” “How did you make ends meet?”

He broke it down for me. And told me all the ways he saves money living abroad.

I did the math on this,” he said. “You won’t believe this, but I pay $42 a year for a 10,000 euro deductible plan.”

Anything after 10,000 euros, he’s covered. “I could get airlifted to John Hopkins if I wanted and that would be covered.”

“You can make about $150,000, tax-free, as an American living abroad.” Here’s how Bobby explains it on the podcast…

If you make $100K (gross) in the U.S, then you’re probably netting less than $60K. Abroad, you can make the same $60K , live tax-free (if you qualify for the “foreign earned income exclusion”), get a housing allowance, pay $42 a year for health insurance, and basically never feel broke again.

I was getting depressed. Because I know I’m not going to move. It’s part of being human. Everyone I look up to, Scott Adams, Dan Ariely, Nassim Taleb, they all say the same thing: people are irrational creatures. Even the idea that we’re being rational, is irrational.

Every time Bobby spoke, I had 10 new questions.

I thought I’d never understand. But then he gave me his secret. And it answered all my questions.

It was so simple. I couldn’t believe it.

Bobby and his son were walking around Estonia. They left Prague, bought a house and had no plans.

Someone overheard them speaking English.

“You’re American?”

They started talking. “What are you planning to do for your kids for school?”

Bobby had no idea.

“I have a son who’s your son’s age. We found a really good school up the hill. There’s a meeting tonight for foreigners who want to enroll their kids.”

Then Bobby told me his secret…

“I figure it out as I go.”

Links and Resources:

Also mentioned:

  • Bobby uses Numbeo.com to compare costs of living between countries

Bobby mentioned these to learn new skills:

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  • This is great stuff! I have more questions too and I can’t believe the interview was able to come to an end lol!

    • Thanks JM. Glad you enjoyed it.

      • Todd Ferguson

        Interesting interview. Living overseas can’t be compared and should be tried once by anyone with an inkling to do so. I thought the interview made ‘light’ of actually being prepared to make the leap. I’ve been an American ex-pat for 15 years, living in the Middle East and Asia mostly. Along the way, I’ve seen more people who didn’t plan the move well and failed than those who planned a little better and made it work well. 90% can be figured out as you go, as long as you have a steady income without working. Trying to move to another country (especially with kids) and not having an income stream (or job) lined up would most likely be a disaster. Word to the wise – Living abroad becomes addicting, in all the good ways. According to studies, if you live abroad 4 years or more, your chances of repatriating to your own country are about 1%. It’s a great life, and though I visit America often (yes, with my two kids) I can’t imagine ‘not living abroad.’

        • Some people cannot “figure out out” as they go along. Some can. I can. It is mostly a confidence issue and generally related to earning an income. Too many people are mentally trapped in their own box about how the world works and how they can live. Breaking free of those mental chains is the first thing that must be done whether you move abroad or not. I have been hustling and working for myself since I was a kid so I never doubted my ability to make money.

          • And there you have it folks. Since childhood.

          • You can make excuses for yourself, or you can take action. That choice is yours alone.

  • christidman

    In selling , you have to evaluate the customer’s risk aversion. It is measured by that person’s ability to risk his own money. Some people back off when the risk exceeds their ability to cover the loss. People like trump don’t know their limits so they bet the farm every time. They are as predictable as dodo birds. They lose big time.

    • Douglas Kelly

      “People like Trump” That’s a remark I’d expect from people with a high risk aversion. And you probably live in constant fear. People like Trump are billionaires. They lose sometimes, but they win most of the time or they wouldn’t be around anymore. It doesn’t matter how many time you fail, it’s about how many times you get back up and go again. I doubt if you understand that concept.

      I’ve been all over the world, and I’ve noticed one major thing: Americans are the most scared people on the planet. After living in other societies, and returning to America, I can feel the fear in the air. Cut it with a knife. It’s a free floating fear of almost anything imaginable and some things that aren’t.

      You are one who knows his limits all too well, and you’ve limited yourself to very little. Predictable as Dodo birds, and you’ll lose big time, every time.

      It’s hard to respect your attitude.

      • SUST

        It’s unfortunate you’ve chosen to show your disrespect.

        • Funny. All I wanted to do with this podcast is to try and figure out what the President is going to do.

          People say Ken is biased. Of course he is! That’s why I figured he would know more than an unbiased person what the President is going to do.

          If I argued with him, that would have been the end of the interview. I sincerely wanted to go from issue to issue and figure out what he wanted to do. I didn’t need to press an opinion. It’s not like I was going to convince anyone of anything.

          I just wanted facts.

          So it’s funny to see all the political arguing here on either side. Don’t people just want the facts? Am I mistaken here?

          • SUST

            My comment was directed at Douglas Kelly’s disrespectful comment to “christidman,” not your podcast! And this podcast is about making full-time traveling work. Ken is not involved. :)

          • You are not gonna know what Trump is going to do because Trump himself hasn’t figured it out yet. He has no plan fixed in cement. Right now he is destroying the Media4Masses by making them impotent. This is his COUNTER-GIFT to them for their GIFT in the campaign. Trump must do this or suicide.

        • Douglas Kelly

          Yes I have indeed. Your comment is worthy of disrespect.

          • SUST

            It was not my comment.

      • christidman

        So you believe that everything will continue as it has for the past 200 years.? I actually believe that Trump knows exactly what he is doing…crashing the American economy. Either he does it deliberately or it goes down in flames. When FDA loses its power to force doctors to prescribe registered drugs the whole medical insurance scam falls apart and local witchdoctors can get back in business selling their herbs and spices.

        Did you spend any time in Turkey?

  • Ash

    Eh…. Of course he wouldn’t feel broke if he had a motor home, 5 cars and 27 motorcycles BEFORE he sold everything. Dude was already very well off before he started. So traveling the world “without feeling broke” is easy for people that have the money to buy a garage big enough to hold 27 motorcycles and 5 cars… You actually mention this in the podcast, and we COULD do it… but it’ll be a lot harder for someone that doesn’t have that type of income. He could AFFORD to do it because he had a nice safety net of money built up. As I said, he wasn’t broke. So for people that are broke, or borderline broke, and they want to start new and move out the country, it will be very difficulty to get started, especially for the first several years… :/

    I think the video in the link below is a bit more realistic for the average person, because he traveled with very little, backpacked, hitchhiked, and had to busk on the side of the road with his guitar for money. He was broke, but he didn’t FEEL broke. I think that is very different. You don’t need LOTS of money to do what the guy below did, but the guy in the podcast could afford to travel the world due to his lifestyle before he started.

    Video I’m talking about:

    • I never claimed to be broke. But certainly not wealthy. I would say upper middle class at best.

    • Here’s a post some might be interested in as a very practical way to get over that hump. http://tynan.com/runway

  • Virginia Reeves

    “I figure it out as I go.” I’ve seen this little ‘mantra’ in other places and there is validity to it. While making plans, setting goals, and putting into practice those little steps can be good – sometimes we have to let life flow.

    • Bobby here. You are correct. You can plan till you are blue in the face, but sometimes you need to go with the flow.

      • mary.rousseau

        I have earned $104000 last year by working online from home and I did that by w­o­r­k­i­n­g part-time f­o­r 3+ h on daily basis. I’m using work model I was introduced by this website i found online and I am so excited that i was able to make so much money on the side. It’s newbie friendly a­­n­­d I’m so grateful that I found out about it. This is what i did… http://registrations37.com

      • I was paid 104,000 thousand dollars previous year by working on-line from home a­n­d I manage to accomplish that by wo­rking part-time f­o­r 3 or sometimes more hrs /daily. I used work model I was introduced by this website i found online and I am so thrilled that I was able to earn so much extra income. It’s so user friendly a­n­d I am just so thankful that i found it. Here’s what I did… http://statictab.com/dk8k8gt

      • Jesse Travis Scott

        Hi Bobby – Apologies for the late question, but I only listened to your episode yesterday. You mention a place in south america, which sounds like “metagene” when you and James discuss it, but I can’t find what place exactly you’re speaking of? Cartegena is the closest I can find. Can you let me know the name of this city/place?

        • It’s Medellín

  • Dorian Gray

    One of the best podcasts. I’ve been dreaming of living in the Philippines, but have never acted on it.

    • Patrick Millerd

      Having lived in Cebu for the last 4 years I would recommend spending some time in different parts of the Philippines at different times of the year. Both lifestyle and weather can be very different!

      Although in most areas you have to enjoy hot and humid all year round!

      The best is the people!

    • Thanks Dorian. Glad you enjoyed it. I urge you to follow your dream and give it a shot. Worst case scenario its not for you and move back home.

    • Brigitta Perez

      I also encourage you to follow your dream, but make sure you pick the area well. I do not recommend Manila. Lived there for 3 yrs. Very polluted, was hard to see the poverty all day around. Any of the islands are beautiful but can be under developed at times. Good Luck with all.

  • Mark Peters

    I live overseas now. I was recruited by a bank and moved my family. I’ve made a mission to check out these guys who “just figure it out as I go”. I know many who took the leap with as little as $10,000. If you have skills you can sell in $, you can live quire nicely, just as Bobby suggested or even better.

    • Thanks Mark.

      • Mark Peters

        You clearly ‘figured it out”! Couldn’t agree more with your conclusions. Great interview.

    • No doubt. If you know how to work the internet that is a major plus. It was fun when it first opened up but has become assembly line boring now. How about seeing where the local people can benefit by skills you have that they need rather than commodities you want to sell. Granted you can sell local commodities that will benefit them and get them into the capitalistic machine. Bill Gates is doing that. Sorry I want to see that machine crumble B4 it destroys all species on the planet. Well it will crumble anyway because western civilization is in the stage of disintegration.- Toynbee.

  • Jean-louis

    No mention of getting to know foreign cultures and locals. No mention of learning any languages (eastern Europeans easily speak 3 to 6 languages. Did Bobby learn Russian?). No mention of local cuisine & habits (fishing & hunting in the winter in Russia is awesome!). Sticked to bottom of Maslow pyramid. Stick with American fellows. Just money focus. But interesting feedback on fear of change. “We are born formated, some end free” French philosophy

    • Yes he is a carpet bagger for sure.No culture, just getting the best deals. Bet he doesn’t read, think, etc. But his practical knowledge is helpful for anyone with a different mind set.

      • Yep, you nailed it. I only speak English, Russian, so-so Spanish and currently learning Latvian. I also only read 3-4 books per month.

        • I have known many multi lingual people. I used to say that they speak all these languages and have nothing to say in any of them. I like the information in this article. But as Foucault says, “Information is not knowledge and knowledge is not knowing.” Reading a lot of books doesn’t mean anything. What books you read does. But the Discourse of this man does not indicate any particular intelligence or culture. I stand with what I said. He is a carper bagger. Would you be willing to provide a list of the books you read last month and a summary? Your own thoughts about the books? Never mind.Thanks for the info tho.

          • Last month:
            The Handmaid’s Tale by Margaret Atwood
            Hardcore Zen by Brad Warner
            The 6th book in the Foundation series (forgot title) by Isaac Asimov

            Definition of carpet bagger:
            a political candidate who seeks election in an area where they have no local connections.
            (in the US) a person from the northern states who went to the South after the Civil War to profit from the Reconstruction.
            a person perceived as an unscrupulous opportunist.

            I am certainly not a political candidate, nor am I from the north during civil war times. Therefore I assume you must think I am an unscrupulous opportunist.

            Tell me again how I am taking advantage of you or any other listeners/readers?

    • I speak Russian, mediocre Spanish and currently learning Latvian. I live as a local and rarely spend time with Americans unless they are travelers visiting me.

  • Joe Sirianni

    Figure it out as you go ? Dude…….that’s called FAITH

  • Linda Dorman

    I think your guest was a little more optimistic than most people experience but he’s right that it’s a lot cheaper to live – and live well – outside the US especially since technology and the sharing economy make it possible. Bobby Casey’s portable skills and disposable assets were vital factors in his ability to start this lifestyle.
    You don’t mention his age, but I’m guessing late-40’s and I think it’s important to note many more of us over 45 are living this way. I’m 56 and living in Asia and Europe with no home base for 2+ years now. As a former corporate expat, living outside the US is the easy part. Building my own online business and not going back to being an employee (with a steady paycheck and benefits) is the hardest thing to do!

  • Thank you for this. I have been on the edge for awhile and this just gave me more incentive.

    • I hope it helps. Glad you enjoyed it.

  • James Buechler

    For yet the fourth times I tried to subscribe to you on itunes. How do I do that? I don’t download shows, I just listen to them.

  • Kayvee

    Great interview

    Where can we get that free report that was mentioned at the end of the interview?

  • Andres Vernazza

    Great episode!

    • Thanks Andres. Glad you enjoyed it.

  • Su Ai

    What is the place in South America he mentioned?

    • wuuk

      Medellín , Colombia. Yes, as in the epicenter of cocaine manufacturing/distribution. It might be different now and he probably lived in a mostly ex-pat nabe.

      • index1000

        its way different, beautiiful city, beautiful people nothing like it was in the days of Escobar. Maybe check things out before spouting outdated crap about a place you have never visited.

        • Freedom fighter

          I agree. Way different, and because of its checkered past, very cheap still. Do not wait until everybody knows it, great locations still available.

    • Yes, Medellin. Really great city. Of course there are still drugs there but there is no cartel crime anymore. 20 years ago Medellin had about 400,000 people. Today its around 4,000,000. All growth from massive improvement in infrastructure, safety and quality of life.

  • Bill Hibbler

    My best friend is from Riga but left there in 1971. I strongly considered a move to Eastern Europe in 2002. It was ridiculously cheap to live in Russia at the time. High speed internet access was difficult to find and that was a necessity for the work I was doing then but that’s less of an issue today. I speak a little Russian, too, but didn’t enjoy Russia compared to many other places I’ve visited.

    It sounds like Bobby’s daughter adapted and made the best of the situation but I never got an impression of what the other two kids thought of the move despite James asking the question a couple of times.

    • No issue now with internet. I get 50mbp up and down on my cell phone. 2nd fastest internet in the world. My youngest loved the environment. My middle son didn’t like living in Riga, but he was also living there during his middle school years when you just hate everything…lol

  • Tim

    The USA isn’t that great anymore. Everything cost a fortune. One illness can wipe your life savings out. Getting old can wipe you out. Nursing homes are a racket.

    • No doubt there. I save at least 10k/year on healthcare alone.

  • Federico Randall

    Men, i love ur site but come on, this guy was already rich n full of resources, he just made a convinient change…thats all, i dont wee much improvement and performance as the title post promised, please no more rich bored adventures

    • Hahaha. Far from rich actually.

  • 2 antinous

    Bobby-can you direct me to where I can buy health insurance (you stated for $42/year)?
    I am in the process of selling/getting rid of all that I own and I want to live in Europe. Thanks.

  • Gustavo Woltmann

    To travel the world, I wish

  • Tolulope

    hmmmm,,,so true

  • Natsmavenus

    Thank you James for the podcast. I always learn something useful from your guests. Too bad this man’s interest in living abroad appears to be motivated solely by the opportunity to live cheap off of these emerging democracies. He never mentioned giving back to the people of his host countries by donating anything – not even his expertise, which would not require him to reach for his wallet – but did mention his 27 motorcycles several times. I have no idea if he even likes these places or the local people. Someone will pay if he’s “airlifted to John Hopkins” on his $42 a year health care plan. James often talks about giving to others with no expectation of return, and good things will come back to you. Perhaps the guest could use a life lesson from James. I think he would be a richer and happier person for it.

  • RoseMart

    Great interview. How about traveling with pets? I often wondered how people travel abroad with pets. It must be difficult. Each country would have their own set of rules, I’m sure. If anyone has info on this, it would be great. What countries are more pet-friendly? Thanks.