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That'a a great question......can anyone think of another industry or occupation to compare it to? An industry not allowed in the USA (unless the govt gets a piece)??
Without a doubt there are tax issues. If you go to Costa Rica or any place else to earn your living, Uncle Sam still wants a post card!
Without a doubt, there have been people charged with criminal complaints that were working at a sportsbook offshore. These people were not targeted as employees. Most of them gave the false impression to undercover agents of the FBI that they were indeed owners. Often in the past, sales people use to say they were the owner to put players at ease with sending their money offshore. This is what got them in trouble.
I guess the biggest test is the Cohen case. If his appeal does not overturn the conviction then we might find the answer to this question relatively soon.
As far as taxes are concerned, since most of us who work offshore are home in the US for less than 30 days a year, we are entitled to, "Foreign Exclusion." This means that whatever we make overseas is tax exempt in the US up to US$72,000.00.
Rich
I think it depends what you do for them. If you are consulting for a book or helping with marketing or something like that it shouldn't be a problem - and that includes even if you live in the United States.
As a Canadian, I don't confess to know U.S. laws but I'd say as long as you have nothing to do with the servers or the taking of bets, that you should be fine. Just make sure you declare all your income.
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