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

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

#292
I know a bit about the subject and here's my advice:

1) Take care of your will and heirs - sometimes it's called "estate planning". There are cheap options online, with the risk of making some terrible mistakes. Hire an attorney with lots of experience doing this, and ask him/her to setup a trust for you and your family. Make sure you fully understand the tax implications of what you're going to setup.

2) The biggest risk of a large sum of money is trying to manage it and allocate it all at once. Imagine that investing or managing money is like a sport, and you have pretty much never trained for this. What would you do? You'd take it step by step. With money, slow down and take a decision at a time.

3) 8M is in the range of "f*ck you money", which means it gives you complete economical freedom for your life, and probably for your heirs too. It's probably wise to maximize for "survivability" of your egg nest, rather than trying to make even more money. Therefore, be conservative when deciding where to invest.

4) Diversify: like redundancy for high-availability IT applications, you need at least 2, possibly 3 quite independent asset classes to invest into (e.g. real estate, stocks, bonds, cryptocurrencies, foreign real estate, etc). Unfortunately, common wisdom about how to properly diversify is debatable to say the least. Spend some time reading and learning and try to come up with something satisfactory.

5) You might hire an investment manager, I am not a big fan of most of these guys, but it might be a way to learn, and you don't need to allocate a huge sum with him/her (perhaps less than 500k?).

6) Make sure you and your wife are 100% aligned with your "money" strategy.

7) Don't make it too public that you own $8M. It's not unheard of in certain places like Silicon Valley, but at the same time, when people know you're rich, they take for granted that you can afford things and that you are supposed to contribute more to other things. Certain relationships become a bit complicated. Just keep it for yourself.

8) Make sure your "IT security" is safe, especially if you will end up owning cryptocurrencies, but also in general.

9) Other than this, enjoy your life. Money is to buy freedom.

10) Finally, if you think you've been given a nice hand by fate, why don't you commit a small fraction of that (2%? 5%?) to doing good for others. Pick a charity, or even better, take a year off and volunteer somewhere with your family. It could be great.

I am no way as rich as you are, but I have enough to be able to "buy" me time with what I have accumulated in the past few years, and that allowed me to do what I wanted to do. It didn't go as expected, but I don't regret it.

At the same time, when you didn't grow up with money in the family, it can be surprisingly hard at times to deal with large sums earned quite quickly, like in your case. The worst parts might be dealing with your partner/spouse, dealing with your friends, and dealing with big recessions where you wipe out maybe half of your net worth.

Good luck.

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

#293
First, congratulations! Now, speaking practically, Act as if you just won the lottery, and proceed accordingly. I'm saying this seriously for the sake of the advice offered in this rather remarkably useful post in reddit about managing a lottery windfall in a way that doesn't ruin you or your family life and relationships. Came to mind right away when I saw this thread, and again, the post is really worth reading through (I have no connection at all to the author, just thought it was very, well written): https://www.reddit.com/r/AskReddit/comments/24vo34/whats_the...

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

#294

Earlier quoted context omitted.

"Also, see if maybe you can develop some hobbies. It can be as simple as hiking or collecting stamps. Preferably one that has a social aspect so you have human interaction." I would avoid material intensive Hobbies where you can buy accomplishment. Unfortunately I am not in a similar situation but if I was I would try to maybe put some effort in to being healthy and not just focusing on beeing stimulated constantly.…

Agreed, it's super easy to pick up a material hobby (like collecting something). Instead, I'd pick up a working hobby. Let's say you really enjoy volunteer work. I'm sure there's a ton of good not-for-profits that need an experienced project manager. Money can't buy happiness. Money can free up your time to explore enriching endeavours. A windfall should be a gateway to really explore what the world has to offer with…

- Make sure my debts are paid, and ensure long term stable income

Totally. No need to carry a car loan, mortgage, Credit card debt anything anymore.

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

#296

You have a life-changing amount of money. I’d take this opportunity to educate yourself on the possibilities now open to you. 1. Take a million of that and move to a nice European city. You can buy a literal mansion in somewhere like Berlin, Warsaw, Prague, Lisbon, Vienna. Comparatively, a million bucks will get you an average normal house in SF or NYC. 2. Take a million and put it toward your children's future educa…

a million dollars will barely buy you an average home in NYC - unless of course you call a 700sft 1 bedroom average.

A million will get you an average little house in a non-sexy part of Queens.

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

#297
Hire a financial adviser - ask friends or relatives with similar net worth about their advisers. A good adviser can give you peace of mind, and help you avoid an awful lot of undesirable scenario's. I would suggest a fee-based adviser with fiduciary responsibility. That person will have a vested interest in preserving and growing your wealth, since their fee is a portion of that growth. Also, congratulations! Celebrate with your family and don't buy any lambos.

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

#298
Do nothing and retire, find some relaxing job maybe. Don't give away, or start having some "brilliant" investment ideas. Figuring out how to make the things work - taxes, health insurance, diversifying assets for security - will take enough time and effort to figure out.

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

#299

Retire. You can live off the interest if invested in mostly stable stuff (so I've heard) assuming you don't have a larger tax bill looming. You may read lots of "awesome coder, great bizdev person" stuff online but 95% of the people out there in Tech are just working on someone else's idea/company bringing home pay. You are free from that now. Be bored for a while and your interests will emerge. Take up a hobby, be a…

Retiring is pretty dull at age 43. Maybe work on something you're into but which doesn't necessarily bring in much money. Personally, also having some money, I'm working on startup idea to fix the world etc which currently brings in zero money but is fun. Maybe it'll turn in to something real later, who knows. By the way re investing I recommend mainstream stuff like blue chip stocks, income producing real estate etc.
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