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I live in the USA and I have an opportunity to sell some used consumer electronics in Paraguay with pretty nice margins. I have a buyer lined up (also a family member on my other side) and have looked into import duties. I would simply purchase, fly in, pay duties on the goods and surprisingly, after duties, there is some reasonably nice money to be made. A family member in brazil is willing to send me about $100,000.00 to bankroll a series of export transactions.

Essentially I dont want to do anything that is illegal, and I'm just very concerned I could do so unwittingly. I have a triangulated series of transfers that perhaps could come across as money laundering.

What are the rules and regulations for a wire transfer from abroad to the USA of this size? Should I report to IRS immediately? Of note, it can be transferred into either my personal account of business account.

To make the issue even more complicated, my uncle in Paraguay deals in cash... he would prefer to give me cash. Is this even manageable when I fly back if its over 10k?

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    Talk to an accountant.
    – Michael
    Commented Aug 17, 2017 at 12:32
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    You can bring in any amount of cash or checks with you when you re-enter the US, but if the total amount is $10K or more, this needs to be declared on an appropriate form before exiting US Customs. That is, you don't check the "Nothing to Declare" box and hand the form to the Customs official as you walk out the door with your baggage and undeclared cash/checks. Commented Aug 17, 2017 at 19:14
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    Also if you deposit (or withdraw) over USD10k cash at a bank/CU/etc they must report it to FinCEN, and most other businesses must report to either FinCEN or IRS. This is a nuisance. Do NOT try to avoid it by breaking your transaction into chunks of 9k or whatever; that's called 'structuring' and is a crime, and the govt can seize your money just because you hid it even though the underlying possession and/or transfer was legal. There numerous Qs on this already, use the search function. And both this and customs is for currency of any country(ies) that totals USD10k after conversion. Commented Aug 18, 2017 at 18:40
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    As for the transfer itself, if you receive income for your sales in a trade or business, you report it on your income tax return at the end of the year. You can deduct your business expenses, including the cost of purchasing or making the goods sold, and you report and pay both income tax and self-employment tax on the net income. If you don't have withholding on this income you are usually required to make estimated payments in Apr Jun Sep Jan (only pay not file the details, which waits until end of year) but the first year you may get a 'safe haven' (again see existing Qs). Commented Aug 18, 2017 at 18:42

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Exactly as was said in a comment, and as often comes up here:

surprisingly DO NOT repeat DO NOT break up a transaction into smaller amounts, in an attempt to make it innocuous.

Surprisingly that act initself - breaking it up in to smaller pieces - is (in a word) illegal in most major jurisdictions and will instantly, immediately, bring you a huge amount of attention and trouble.

DO NOT break it up. It is called "structuring", it is a crime, you will instantly be caught and likely do jail time, and they'll confiscate every penny.

Again, on the other hand, it is 100% ok, normal and commonplace to send 10, 50, 100 thousand bucks around for transactions like this. Even in cash - lots of folks deal in cash (say, gem dealers). Absolutely no problem. it won't even be noticed. There's just a form to fill in at the airport.

You have to declare every item to customs. If you carry cash (or anything like cash - gold, certificates, etc) across borders, you do have to fill in a form declaring that. Obviously you have to pay duties on everything at both ends (if relevant) and state and federal income tax on everything.

Again the surprising short answer to your question (often asked on here),

1) There is utterly no problem whatsoever, with sending around 10, 50, 200 thousand bucks. Even in cash.

2) Absolutely do not try to "break it up" to "avoid attention". This is an actual crime called "structuring." You will instantly, within minutes, be detected. You will be severely punished.

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