Set up trusts for those I care about. Donate 10mil to charity (like St Jude’s). Take 5 million and just spend as I see fit (which probably means I’ll end up with 4.5 million sitting there for a while. The rest I’d invest and live off the interest and dividends.

I’ve thought a lot about this :)

Mmm… eternal poutine fund…

Beyond food for myself, I’d love to pay for programs and services I’ve graciously been given access to like WinRar, Wikipedia, The Internet Archive… People have shared with me and made my life better, I’d love to return the favour en-mass.

I’d invest everything else into supporting educational endeavours.

We have a whole plan for this, not because we actually believe it’s going to happen, but because it’s fun to think about.

Plan involves

1. Gifting close family members wnough money to pay for their mortgages and other debts
2. setting up an investment envelope from which we can gift shares, which will pay yearly dividends and gifting those to family members. Idea is to ensure everyone will have some money to spend, but prevent squandering of the money.
3. I would probably start my own company, have a few ideas. Wife would probably move to working part time (it’s fun to work, but it’d be nice to work a little less)
4. There is an ancestral home of my family which we have not had the money to maintain, I would hire people to fix it (and probably spend time fixing it myself)

Pay off my mortgage and car loan. Invest the rest in index funds. Pull out enough to keep my current lifestyle without working.

A money market account, and then I’d live off the interest.

For me I’ve always loved flying, and have wanted to get my pilots license since I was a little kid. So the first thing I’d buy would be a little Cessna, and then I’d take my time and do a “road trip” to see the whole country by air.

I live in a co-op, we currently have two houses but we unfortunately rent both from landlords. We’re hoping to eventually buy properties, either our current ones or something else, but it’s very hard with the current market and of course the fact that most of us aren’t very high-earners to begin with.

With $100M, screw buying, I am getting a custom designed and built co-op! Features like industrial kitchen, many varied common spaces, and just being able to own our property and be saved from the landlord rent greed. I have to imagine I’d have plenty of money left after, but this is the top of my list for sure

Get a second car for my family and buy a house… God damn this feels bleak.

First thing would be to upgrade to a house from our townhouse, and pay off the mortgage and car loan. Then we’d buy our close friends and family new houses too, and bringing them on a really nice vacation. After we’d probably save most of it for now.

Some shares on the market.

Realising I didn’t actually answer the question in my other comment….

The very first thing I’d buy? Probably something to celebrate with. A really good dinner out with a glass of expensive dry champagne (then move on to the best bottle of red that the restaurant had to offer!)

Maybe 100K in gold, just as a backup if its ever needed.

I’d speak to a financial advisor to make sure I can put away enough money that we’d never have to work again while maintains a quality of life at least matching (but realistically with that kind of winning a bit higher!) than we have now)

After that it’s all’s about giving it away to family and friends (and charities).

I dream about winning the lottery a lot and my thoughts are always about time and experiences. I don’t think I’d ever really indulge in lots of overly expensive stuff. I just want my time back to spend with my family (and with myself!) rather than having to lose such a large portion of my life to work.

Oh I’d also spend time (children allowing) travelling (nice lottery winner travelling) - I’d love to see more of the US national parks plus the Nordic countries.

Quietly pay my debt, put aside enough to retire comfortably, a little to buy a decent house and some cool cars and vacations slowly as I can come up with justifications for why I could afford them, and then donate the rest to charities, likely very established ones that can handle that kind of thing gracefully, I really don’t want to make it my life’s work to vet charities or worry about the people I hired to do it. Might be cool to set up a small investment fund for cool videogame projects I want to see happen to their fullest.

I’m not telling a soul I won more than $500 in a lottery apart from a lawyer if necessary to protect my identity. I know my immediate family would be cool about it as long as I always paid for dinner, but who knows about others.

The more fun answer? That Yellow/black Ford GT that I see at car shows around here, a replica of the Bullitt Mustang, and an Alfa Romeo Giulia GTA. I’d also be a club member at the local track with my own garage in the paddock.

Assassins that kill people who organize lotteries.