[thehnguy]

Agreed with the bogleheads suggestion. I’m a lawyer who does some consulting to people in similar situations, and the mistake that everyone makes is thinking that because it’s a lot of money somehow it has to be treated differently. This is just plain wrong.

Resist the urge to hire a fancy money manager or do anything different beyond a celebratory dinner with your family.

Don’t tell anyone beyond your wife and very trustworthy family about this. Otherwise,you will quickly have lots of “friends” and family members who “love” you.

Going forward with work is a personal decision. Obviously, you don’t need to. A tried-and-true conservative investment approach will pay you sufficient income for the rest of your life (and our kids through college, and everything else). But it’s tough to stop working. Anecdotally, I’m about half retired (on a lot less money) and it’s a big challenge.

I’m getting long winded. For now, resist the urge to do anything special, anything too different.

[pmart123]

"Don’t tell anyone beyond your wife and very trustworthy family about this. Otherwise,you will quickly have lots of 'friends' and family members who “love” you."

I completely agree with this if he had won the lottery. Money found is different than money earned. In this situation though, the OP picked the right startup, put work and effort into making it successful, and was financially compensated for the risk and effort he took. I would say he should own his success; the money is rightfully his.

[b_tterc_p]

It’s not really about owning anything. It’s thieving friends of family who will hold it against you if the wealth is not shared on account of your apparently deep social bond, if not trying to wrings it out of your wallet outright.

[pmart123]

I think in practice though, if you act that you "earned it", it is much harder for people to assume they can ask you for it. You here a lot about lottery winners going broke, but you don't hear as much as startup employees on exit eventually going broke. This may be just a result of education and income levels, but I also believe that people don't mind asking you for money if it seems like it came to you through luck and not effort.

[ansy]

The justification isn't that OP came by the money unfairly, it's that because he has so much he doesn't need it as much as his friends and family need it. "Oh, can I get $20,000 for my business idea? Will you help send your niece to private school instead of state school? I'm paying 25% interest on this credit card debt, can you give me the money to pay it off?" etc etc. Everyone from his parents to that one guy he knew in college will want to solve their "small" money problems with OP's windfall, because to them he'll still be a millionaire and never have to work again. What eventually happens is OP will have to start saying NO to people then they will resent him and it will change the dynamic of their relationship. Or he could just keep his finances to himself and not bring this on himself. I'm not saying he shouldn't be able to help anyone who really needs it. It's just in his best interest to not advertise how much he really has to other people.