Ask HN: What to do after $8M (all cash, post tax) exit?

I think most everyone in the sub-$25M bracket is better served paying a broad-based index fund 0 to 4 basis points for VTSAX or similar and using fee-only planner/advisers for tax, estate, and investment advice.

Completely agree that if OP wasn't previously a skilled investor with a track record of beating the market (extremely unlikely), that they shouldn't now try to become one.

With this amount of money, they've "won the game" and have no need to beat the market. They only need to match the market over the next 50 years. That can be done very simply, reliably, and cheaply.

I recently met a friend's father-in-law at a party. He seemed like a super modest guy, and then I realized he acquired a similar windfall twenty years ago. He kept working at the same company, and then jumped to a project manager role at a new company. Even after major back surgery, he kept working like an average joe (and seemed to enjoy his job). Outside of family vacations, he has only made one major purchase from his fortune - a crash-pad apartment in the Upper West Side that ended up doubling in value since the nineties.

At the time, I thought he was a bit eccentric; maybe even a workaholic. Especially after reading this thread, I think he did absolutely everything correct.

Some people experience very real guilt/depression when a windfall happens "I don't deserve this" "why me" "shoulda been someone else" etc, not unlike survivor's guilt.

First thing you should do is something fun. Second thing you should do is something fun. Third thing you should do is something for someone else. Make that take at least year. Don't spend more than $500k on it. By then you'll know what you want to. Oh, and don't forget to be humbled by how insanely insanely lucky you are.

1. Get an attorney to make sure you don't get screwed in taxes or by some wanker trying to make a dime.

2. As you described it, I would say invest all of the money. If you're fine living humble, then use the money as security. With eight million you can pretty much comfortably. A low risk investment like a CD can provide you with roughly a 120K (@1.5% interest) salary.

3. Continue to work. But rest easy knowing that if you have a trash job, you can quit and find a new one without worrying about how you're going to provide.

4. Pay off everything.

5. Find a couple decent indulgences. Buy a Corvette or take the family on vacation. But don't go crazy. Spend 100k.

Lastly, I think being too comfortable makes people unhappy. Personally the times when I am most secure, are the times I am least happy. Take up rock climbing, skydiving, marathon running or anything that makes you uncomfortable (preferably without destroying yourself). It'll keep things in perspective. I rock climb, canyoneer and run Spartan races and those make me far happier than any amount of money I have earned thus far.