Liberty Entrepreneurs – Tax Tips for Digital Nomads with Bobby Casey


Today’s guest is Bobby Casey from www. He’s one of those guys who has figured out the tax system for digital nomads; including us Americans. Growing up in a household full of accountants, Bobby has been around taxes, using corporate structures and the offshore financial world his entire life.

Are you confused and maybe frustrated with trying to figure out how to best structure your various business and incomes to best protect the money you’ve voluntarily earned? When should you choose an LLC vs a S-corp or maybe file your LLC as an S-corp.

This episode is a must listen for those who have decided to travel the world and work online.

Pay your taxes. Just learn the system and take your legal credits and refunds. Living as a Digital Nomad has tons of benefits and the government will subsidise your living abroad if you learn the rules.

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Meet the hosts

Ashe Whitener is the founder and host of the Liberty Entrepreneurs Podcast which aims to provide an alternative perspective to achieving individual freedom through the creative, entrepreneurial process rather than through the tried and failed process of politics. Ashe has two BS degrees in Engineering and is also an original member of Peter Schiff’s Euro Pacific Bank where he is currently the Head of Business Development. Much of Ashe’s experience has come during his time living in Panama and he continues to consult global teams on various projects including tech startups and offshore asset protection.


  • I debated whether or not this should be posted in the history discussion category as today may indeed go down as a tipping point in the game of government intimidation. Could we bee too hopeful to think that the next significant confrontation could be with the bureaucracy everyone loves to hate?

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  • The “Tax Honesty” movement has demonstrated a few things to a lot of people.  To cover a lot with a few words, I’ll put it this way:  The IRS breaks its own rules in order to rob us through deceit. Some people (Irwin Schiff, for example) have suffered because they attempted to protect themselves from the rule-breakers.  There is now a theory popular among liberty-minded people that the government is too corrupt and powerful for anyone to succeed in an effort like Irwin Schiff’s.  There is also some good evidence showing this theory to be wrong.  It’s available at Peter Hendrickson’s website, I think that a lot of bureaucrats feel and believe that they are helping society.  This leaves them open to consider fixing situations in which their bureaucracy is breaking its own rules.  And let’s face it, there are some rules that can actually help liberty.  Perhaps the loads of evidence that Hendrickson has on his site can be explained by the presence of such “good-hearted” individuals in the bowels of the IRS. In any case, if you can, please entertain the possibility that the US Income Tax is not being administered honestly.  Consider that maybe, just maybe, in the gargantuan tangle of words called “Title 26,” the legal meaning of the law as it applies to most people is not coercive at all.  Maybe, if it were properly applied, the government would be a nuisance like neighbors who let their dogs poop on your lawn, instead of a nuisance like cancer in your lungs.  It could be true.  I think it is true, and I think that failing to follow all the twists and turns that Hendrickson uncovered to see for yourself that it is true kind of justifies you still being enslaved to a government that steals from you in order to cause havoc all over the planet in a massive deception that justifies its existence. If we want to honor the goodness in all people, including those who have been tricked into serving evil, we can do so by understanding the rules they think they should be following, and using them to protect ourselves from enslavement.

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  • It can be a challenge to keep up with all the taxes one needs to pay throughout the year, and than to deal with all the paperwork that needs to be filed can be frustrating. What would be a good way to simplify the Tax Code? Below is a list of some of the taxes that we the people need to pay, or at least we experience their effects at one time or another. -Medicare, Medicare, Social Security, Federal Inocme Tax, State tax, Local Tax, Corporate tax, Sales Tax, Property Tax, estate tax, alcohol tax, tobacco tax, gift tax, tariffs on imports and exports, etc. Would a simple flat or consumption tax do the trick?

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  • I’ve just recently blogged about Insidious Government Encroachment which I believe would provide the basis on a useful discussion here.   I’d be interested and hearing the views and experiences of others from this group.

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  • I recently started looking into the nature of land ownership. I was under the impression that land ownership was absolute- a person is free to lease, sell, rent, put up for collateral, or destroy their land as they see fit. Where, then, does the right of the state to tax and seize fit in? The common sense answer- that ownership is not absolute- is mostly correct. But it’s quite interesting to look into the history of why land ownership is not absolute. The ownership of land that isn’t subject to any higher authority- no state, no landlord, etc.- is called alloidal title or title in alloidum. In feudal times, the only person to hold alloidal title was the feudal lord. He was considered sovereign over the land. No one else had a right to interfere with his use of the property. Other types of ownership that the lord bestowed allowed the people on the land to exercise certain rights, such as the right to sublet, or the right to put the land up as collateral. In modern nation-states, the sovereign (i.e., the government) still exercises exclusive alloidal title. That is to say, you don’t own the land, the United States does. You can’t ever remove the land from their jurisdiction because you don’t have that right. Moreover, as the sovereign, the government retains the right to tax land, seize it through eminent domain, and steal a portion of the land in the event that there is no will. What exactly do landowners own then? They own an interest in real property. When land is bought and sold, what’s actually being legally exchanged is the interest in the land, not the land itself. This is called fee simple ownership. Interestingly, the word fee in this concept is a descendant of the word fief, or land held on the condition of feudal service. Under fee simple ownership, the government- be it feudal lord or “we the people”- retains full ownership of the land, while the subjects of the government are free to exchange title to the land. Never does the land cease to belong to the sovereign, and thus it’s power it protected. As I researched the nature of land ownership, and it’s descent from English common law, the blind justifications made more sense. Of course, they’re not morally right (Thomas Jefferson was in favor of alloidal title) but they make more sense. I’d like to know your thoughts on the matter, and if there’s a professional real estate lawyer who could contribute more to the conversation, that would be great.

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