I don’t know why stuff like this keeps me up at night but let’s pretend you just won some obscene amount and there’s a lot of people you’d like to set up for life. Let’s say after taxes you have $300m in your account
You can give someone up to 18k a year without incurring a gift tax and while that’d definitely be a nice bump to their income, you still have way more money than you know what to do with. So what’s the smartest way to hook them up?
A couple of options I’ve considered are:
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Give them a lump sum of $X million. They eat the taxes the first year and handle the savings themselves.
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Create a company and hire them to “work” one hour a month for a big salary. If you put $25m in an account, the interest covers the salary. They get a steady bonus income with the added bonus of getting the best insurance available. Is that legal?
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Set up a “shared” checking account they can use to pay for…whatever. But would these expenses count towards the gift tax? I do not know.
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Buy houses and let them live there rent-free. I don’t really like this one because I don’t want to be a lord to my friends and family.
For the record, I did not win the lottery. I don’t even play it. I’m just working out the details in a fantasy world for some reason
Don’t try to cheat the government. make sure you can say either you reported the large gift for tax purposes or the total is under 18k., if you must cheat you can take them on vecation and they use your gear for free but the plane ticket, meals and anything that could look like a gift is under the limit.
tax fraud is something the irs takes serously and you never know when they look. Plus you are not sympathetic to a jury so prison is likely for you.
if you give anyone more than 10k in a year (well under the limit) have your accountant deliver it all so there is plenty of evidence that you are not cheating. If you want to give over 18k have your accountant figure out how to do withholding so you friends don’t have a tax surprise.
What about shared credit cards?
same thing, they are lakely to audit them and see if they are being used to cheat. You can use them but either count everything as a gift or have good records that whatever isn’t a going to whoever.