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

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421–430 of 531 posts

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

#421

The thing that concerns me is that "I do not think I have any real hobbies." I suggest continuing to work, but perhaps being pickier about where you work. Perhaps there's a dream job you've always wanted to do that up until now wasn't feasible because it doesn't pay enough, like fireman, park ranger, teacher, musician, etc? The key here is to have an obligation (people depend on you) and social interaction. Also, see…

It can be equally detrimental to your physical health as well.

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

#422
post #55

Speaking as someone who made a decent pile in cryptocurrency: 1. Don't ride on the stocks forever. You'll feel it as a windfall now, but it's an investment. You invested in the company, and it paid off, so you should probably part ways and start a new chapter, since the company's fortunes can change quickly. Every investment comes with risk and the more you have in one investment, the more you will feel that risk - s…

OP said the $8M hit his account after taxes.

Not next years taxes. Hence, why tax shelters exist.

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

#423
post #299

Earlier quoted context omitted.

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…

I "retired" in my mid-20s for about 3 years. I only went back to work when I ran out of money. Describing complete freedom as "dull" is an insane concept to me. You can work out, read, watch TV, go to coffee shops, cook, or even just sit around all day with no commitments.

You didn't retire, you just quit working until you went broke.

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

#424
For now, get a new job if a similar sort. Bank the money in several relatively safe places (insured accounts and CD's. Let it sit and earn even trivial interest for the moment. Maintain the same lifestyle. Make no substantial changes for at least a year. You and your wife should have a many heart-to-heart talk about what your ultimate goals in this life and the next are, and how your windfall may or may not help that. Don't rush.

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

#425

Earlier quoted context omitted.

You should NOT have 8 million in a checking account.

Because FDIC only insures $250K? SIPC only covers $500K somewhere like Schwab[1] - or do you mean because you think it's terrible not be earning something on the $8M? Presumably that's enough for anyone to live out the rest of their life on comfortably... 1: https://www.schwabmoneywise.com/public/moneywise/essentials/...

I mostly meant for safety. You want it split up for many reasons... so you can have the FDIC or SIPC insurance, so you don't have to worry about losing access to the account via fraud, etc.

It would be ok for a short term to keep it in checking or savings accounts, but don't put it all in one.

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

#426
Practical advice aside, take a step back and bask in the pleasure of the wonderful, unambiguously lucky thing that's happened to you. It's OK to feel excited and happy about all the freedom and peace of mind you now have.

Loved one gets sick? You don't have to think about money. Kids need something? It's taken care of. Getting 8 million dollars out of thin air is amazing and you shouldn't let your anxiety and self doubt stop you from feeling happy for a while.

You can figure out what to do with it later. Just enjoy having it in your checking account and looking at it every few hours in your bank's app. Buy something frivolous that costs $10,000 that you've always wanted. Give each of your family members a great gift. Donate $10,000 to something that matters to you. Let yourself spend $40,000 or so to celebrate, and then be responsible with the rest.

Congratulations, my friend!

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

#427
I've been in that situation since the 1980s. I put the money into T-bills, back when they paid 7%. Now it's mostly in brokered CDs and index funds. I still have about as much money as I had back then, although I haven't quite kept up with inflation. Brokered CDs are useful because you can spread them out across multiple banks and get the $250K FDIC guarantee at each bank.

Most people who get a lot of money all at once blow it within 7 years. I found "The Challenges of Wealth", by Domini, to be useful.

The trouble with investing is that you're competing with people who are smarter than you and do it full time with other peoples's money. Not that they do it very well. VC funds, as a class, lose money. So do hedge funds. There really aren't many good investments right now and there's too much money chasing them. So go for safety, not yield.

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

#428
Having been in your shoes, and having had many friends in a similar place, I can only share what did and didn't work for us.

Diversifying was a positive for everyone who did it. John Doerr's advice to a friend was 'sell half' and diversify that. Because of the dot com crash (which may have been an anomaly) the folks who diversified completely (sold it all and moved into a balanced portfolio) did better.

Not changing your lifestyle. You have a 'burn rate' just like everything else (car payments, house payments, tuition bills etc). Leave that alone and your life will continue as it has, only more securely. One of the folks I know switched over to the lifestyle of the 'rich and famous', lots of parties, upgraded house, new cars, vacation trips all around the world. Burned through all their wealth and when it became obvious they had to go back to work, was in the place of going to people who had known them as the rich playboy type, and really impressing upon them how much they needed a job. It wasn't fun for them.

I would recommend you work with a financial adviser, or take a class at a community college on the basics of finance, or both. Back in the dot com days when I thought I was going to be a zillionaire I took the Forbes Wealth Management home study course. It was like 30 cassette tape lectures and a workbook. It did a good job of covering the foundations so that I could understand what people were talking about when they were comparing various options.

Put some aside for your kids college, giving them a debt free college education has a strong positive impact on their future success.

Sleep better and take care of your health.

EDIT: And talk to a tax accountant. Seriously. Moving around money in the "wrong" way can expose you to serious tax liability that might be surprising to you come April.

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

#429

I came into a windfall about a year ago. I found that it's easy to fall in a rut. Having so much money made me feel like that what what other people perceive as the biggest thing about me. I miss the praise and respect that a job well done gave me, that I had while working. After retiring, it's easy to think that, besides the money there is nothing worthwhile about me. Then there is the question about what to do when…

Maybe don't associate your existence with programming, tell them you're a guy with interesting hobbies and wide knowledge who just happens to do programming to empower people to do things/pay the bills/insert narrative here.

As with everything, it's more about the perspective and delivery than actual message.

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