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

  • ScrubblesEnglish
    37•5 months ago

    / 4. You will be encouraged to hire an investment manager. Considerable pressure will be applied. Don’t.

    Investment managers charge fees, usually a percentage of assets. Consider this: If they charge 1% (which is low, I doubt you could find this deal, actually) they have to beat the market by 1% every year just to break even with a general market index fund. It is not worth it, and you don’t need the extra return or the extra risk. Go for the index fund instead if you must invest in stocks. This is a hard rule to follow. They will come recommended by friends. They will come recommended by family. They will be your second cousin on your mother’s side. Investment managers will sound smart. They will have lots of cool acronyms. They will have nice PowerPoint presentations. They might (MIGHT) pay for your shrimp cocktail lunch at TGI Friday’s while reminding you how poor their side of the family is. They live for this stuff.

    You should smile, thank them for their time, and then tell them you will get back to them next week. Don’t sign ANYTHING. Don’t write it on a cocktail napkin (lottery lawsuit cases have been won and lost over drunkenly scrawled cocktail napkin addition and subtraction figures with lots of zeros on them). Never call them back. Trust me. You will thank me later. This tactic, smiling, thanking people for their time, and promising to get back to people, is going to have to become familiar. You will have to learn to say no gently, without saying the word “no.” It sounds underhanded. Sneaky. It is. And its part of your new survival strategy. I mean the word “survival” quite literally.

    Get all this figured out BEFORE you claim your winnings. They aren’t going anywhere. Just relax.

    / 5. If you elect to be more global about your paranoia, use between 20.00% and 33.00% of what you have not decided to commit to a family fund IMMEDIATELY to purchase a combination of longer term U.S. treasuries (5 or 10 year are a good idea) and perhaps even another G7 treasury instrument. This is your safety net. You will be protected… from yourself.

    You are going to be really tempted to starting being a big investor. You are going to be convinced that you can double your money in Vegas with your awesome Roulette system/by funding your friend’s amazing idea to sell Lemming dung/buying land for oil drilling/by shorting the North Pole Ice market (global warming, you know). This all sounds tempting because “Even if I lose it all I still have $XX million left! Anyone could live on that comfortably for the rest of their life.” Yeah, except for 33% of everyone who won the lottery.

    You’re not going to double your money, so cool it. Let me say that again. You’re not going to double your money, so cool it. Right now, you’ll get around 3.5% on the 10 year U.S. treasury. With $18.2 million (20% of $91.2 mil after your absurdly generous family gift) invested in those you will pull down $638,400 per year. If everything else blows up, you still have that, and you will be in the top 1% of income in the United States. So how about you not fuck with it. Eh? And that’s income that is damn safe. If we get to the point where the United States defaults on those instruments, we are in far worse shape than worrying about money.

    If you are really paranoid, you might consider picking another G7 or otherwise mainstream country other than the U.S. according to where you want to live if the United States dissolves into anarchy or Britney Spears is elected to the United States Senate. Put some fraction in something like Swiss Government Bonds at 3%. If the Swiss stop paying on their government debt, well, then you know money really means nothing anywhere on the globe anymore. I’d study small field sustainable agriculture if you think this is a possibility. You might have to start feedng yourself.

    / 6. That leaves, say, 80% of $91.2 million or $72.9 million.

    Here is where things start to get less clear. Personally, I think you should dump half of this, or $36.4 million, into a boring S&P 500 index fund. Find something with low fees. You are going to be constantly tempted to retain “sophisticated” advisers who charge “nominal fees.” Don’t. Period. Even if you lose every other dime, you have $638,400 per year you didn’t have before that will keep coming in until the United States falls into chaos. Fuck advisers and their fees. Instead, drop your $36.4 million in the market in a low fee vehicle. Unless we have an unprecedented downturn the likes of which the United States has never seen, should return around 7.00% or so over the next 10 years. You should expect to touch not even a dime of this money for 10 or 15 or even 20 years. In 20 years $36.4 million could easily become $115 million.

    / 7. So you have put a safety net in place.

    You have provided for your family beyond your wildest dreams. And you still have $36.4 million in “cash.” You know you will be getting $638,400 per year unless the capital building is burning, you don’t ever need to give anyone you care about cash, since they are provided for generously and responsibly (and can’t blow it in Vegas) and you have a HUGE nest egg that is growing at market rates. (Given the recent dip, you’ll be buying in at great prices for the market). What now? Whatever you want. Go ahead and burn through $36.4 million in hookers and blow if you want. You’ve got more security than 99% of the country. A lot of it is in trusts so even if you are sued your family will live well, and progress across generations. If your lawyer is worth his salt (I bet he is) then you will be insulated from most lawsuits anyhow. Buy a nice house or two, make sure they aren’t stupid investments though. Go ahead and be an angel investor and fund some startups, but REFUSE to do it for anyone you know. (Friends and money, oil and water - Michael Corleone) Play. Have fun. You earned it by putting together the shoe sizes of your whole family on one ticket and winning the jackpot.