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:

  1. Give them a lump sum of $X million. They eat the taxes the first year and handle the savings themselves.

  2. 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?

  3. 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.

  4. 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

  • @Lost_My_Mind
    10•2 months ago

    I would think option 2 HAS TO be legal, except, you gotta modify it slightly. You don’t claim they work one hour per month. You pay them a yearly salary. And their job is to “entertain you”. Essentially you’re just paying your friends to hang out, for an unspecified amount of time every year. Which in practical terms is just you giving your friends a paycheck for the sake of giving your friends a paycheck, and sometimes you hang out. I swear to god, this HAS TO BE the basis of Adam Sandlers whole career. He makes movies where he just happens to always hang out with his friends, and somehow other people enjoy the movies too. But mostly it’s him hanging out with his friends.

    Option 4 could work too. But here’s what you do. You hire a landlord. You tell that landlord "Anything they want done, you’re in charge of getting it done. ASAP. I don’t want to hear one peep out of them not getting whatever fixed. That way, they think of the landlord as the landlord, and you as just that friend they have who happens to own the houses they live in rent free. But they don’t think of you as having power over them. That’s what the landlord manager is for.

    You could also buy an old hotel, fix it up, and have it serve as a homeless person shelter. I mean, this doesn’t have anything to do with your question, but if we’re just throwing money around, why not?