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

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211–220 of 531 posts

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

#211
post #172

Put most of it in the stock market. Set aside some cash and use it to improve your everyday life whenever you feel like it. For example, don't fly Economy class if it's crowded and uncomfortable. Spend your holidays in a nice place, better hotel. Eat at better restaurants. But a safer (larger?) car. Do NOT hire a wealth manager or go to some private banking advisors.

this is probably some sort of contra-indicator when average joe off the internet recommends Putting most of your money in the stock market. We must be near the Top of this bull run. This bull market is almost 10 years old. We are overdue for a "breather".

You can’t time the market, so either advice is just as wrong/right. Though the stock market will probably be higher 10 years from now.

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

#212

Amazing how many people think $8M is enough to retire, or even that you'd want to. Go travel the world with the family for a while. Clear your head and have a good think about the future.

Are you arguing $8M is not enough to retire on?

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

#214
post #172

Earlier quoted context omitted.

this is probably some sort of contra-indicator when average joe off the internet recommends Putting most of your money in the stock market. We must be near the Top of this bull run. This bull market is almost 10 years old. We are overdue for a "breather".

Haven’t you been paying attention? We’ve been breathing for the past two months. My tech stocks have lost over $120k of value since September highs, in just two months.

Ha ha, I sunk a few $k in NVDA at $235, thinking they would not be affected by crypto currency (since most people use AMD).

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

#215
post #68
post #35

Earlier quoted context omitted.

"Start a business." Um, he has no need to work. Why would starting a business be the most important thing to do? Basically, he can find out what sensible or quirky thing he likes and do that - just as long as it does not cost more than a middle class income can support. If he's entrepreneurial then sure, business. But I see nothing wrong in spending ones life painting, sculpting, doing maths or science or volunteerin…

Idle hands are the devil's workshop. Having no passion and nothing to do is a sure way to lose everything and ruin your otherwise established life. So better to get to work on your own project now without the fear of going broke. Painting and sculpting, science or volunteering are fine if the person loves it. Otherwise he'll be happy doing what he's been doing all his life before this moment — programming, creating h…

As someone who's pretty idle, the worst (and only bad) part is everybody telling you how something must be wrong. Like people can get outright hostile and say pretty mean things. Everybody's completely fine with you not doing much, but if you actually say you're not doing anything instead of coming up with a random answer they go nuts!

Which I must admit I enjoy in a weird way.

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

#216
post #105

Lots of advice to put your money in the stock market. Have you seen the stock market this year? Don't get me wrong, the stock market is a perfectly great place to park your money, and it's basically back stopped by the US government. My suggestion is look to invest elsewhere. Invest in real estate, invest in businesses. The latter, as you now know, can create much more wealth than the stock market. The end goal of th…

This is full of bad or not helpful advice.

> Lots of advice to put your money in the stock market. Have you seen the stock market this year?

Investing a large sum in the stock market like this is not meant to make quick money, it's for the long term. If you invest in funds that follow the S&P500 it's statistically going to bring solid returns over the long term. This will allow you draw a salary from the returns keeping the principle intact.

> Invest in real estate, invest in businesses.

Investing in real estate and businesses should be a small piece or even hobby until you really get a grasp on it. It's an easy way to lose a lot of money.

> The latter, as you now know, can create much more wealth than the stock market.

It can but again great reward = great risk. Angel investing is a full time job in itself and unless you have the right connections with the best companies it's very difficult to do the right deals where the 10x returns happen.

> Hiring an advisor could be a good idea - but make sure you know their fees.

Not just know their fees but make sure it's a fiduciary and not just a broker. A fiduciary advisor is legally obligated to put your best interest first.

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

#217

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…

"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 without limitations.

My top things that I would do in this situation:

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

- 1 hour minimum workout every day

- Be outside as much as possible

- Learn new applicable skills (home or auto repair, woodworking, music, etc...)

- Possibly go back to school

- Play video games

- Read more

These are all things that I try to do now, but don't have the time because of work or debt.

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

#218
I recently netted $16m from the sale of my startup. Makes for a similar situation.

The boggleheads advice is sound.

You need a CPA for taxes.

Get an estate attorney for a proper will and trust (especially if you live in CA).

Consider better liability insurance. I went for $10M.

You could put your assets into low risk cash management accounts for a while to give yourself some time to think. Think money market or similar.

I ultimately did hire an investment manager but only because I needed the psychological grounding to ensure I didn’t do anything stupid out of the gate. Check references. It doesn’t have to be a lifelong relationship but it helped me.

That said, you can manage your own investments if you have the right temperament.

Don’t tell anyone unless you absolutely have to. It was obvious for me and it does make things weird with some people.

The 4% rule is probably too aggressive for you at 43.

You’ll find that having money makes work optional. I find that helps me enjoy working more than I ever did before now that it’s fully my choice what I do everyday.

Just keep calm and don’t rush into anything.

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

#219
This is a great thread. Throwaway also. Gonna write some stream-of-consciousness here, because I have to start my work day, but I personally made approx. this amount from an exit, and it has gone very well for me and my family (wife + 3 kids). Some additional fine-tuned advice of what worked for me: (1) don't be afraid to spend money - high hourly rates - for a good accountant and good tax attorney. (2) if I were you I'd sign up for a couple different brokerage accounts (e.g., Charles Schwab and one other) and split the money between them. It takes almost no time to do this, and it's nice to have some diversity there in case something catastrophic happens to one of them and your assets are locked up for a long time while it gets sorted out. (3) as others have said, just buy US treasuries (interest rates are good right now) while you sit back and think about it. (4) Eventually if you're not into picking things yourself, you'll just want some healthy mix of asset classes, which (5) you'll learn about by reading some books. (6) Those brokerages will put someone on the phone with you and help you buy the treasuries, if that's confusing. (7) The one thing you want to avoid is letting the brokerages sell you their own personal wealth management. Everyone from your bank to your brokerage will try to sell you the "we'll help you for 1% of your money per year" -- avoid this. Suddenly 10 years have gone by and $800k-ish of your $8million is in someone else's hands, who simply threw darts at a dartboard and did their best to obfuscate their performance during bad times. (8) AVOID PRIVATE INVESTMENTS. Unless you're a professional private equity investor, don't buy a piece of that friend's restaurant, that store that's opening up, that tech startup, whatever. This money tends to disappear. If you're ok losing money to support your cousin who's starting a new company, just give them some money and be honest to yourself and them about the whole thing (not that I advise this either, but don't confuse charity and investment.) Just don't invest in private stuff. The problems with private investments: (a) you lose all liquidity, (b) markets aren't efficient so you can actually do a veeeeery bad job, (c) it can get personal and/or skeezy. So seriously, avoid any kind of private investments. (9) Avoid starting your own business and pouring all your money into it. People tend to burn through windfalls in that way and regret it. (10) Don't race into fancier real estate. (11) Make no lifestyle upgrades at all during the next year. (12) Take your time with charities. It can be a fun family project in the years to come to pick charities together. You'll have income in many years from this money, so you're not missing an opportunity for deductions by not giving money in the first year. (13) OH ! When signing up for brokerages, don't enable options or margin trading. In addition to this being dangerous for you, I believe it allows them to be funky with your cash and holdings, and it complicates your relationship with the brokerage should they or a bank they work with ever go under. (14) don't rush into estate configuration, just start with a simple will. Then consider trusts and things like that in future years. From my and my friends' experiences, they tend to overcomplicate things. (15) TELL AS FEW PEOPLE AS POSSIBLE. (16) Keep working, but only on something you enjoy. (17) Stay or get in shape. Your body is more important than money.

Seriously, AVOID PRIVATE INVESTMENTS.

Kobe Bryant on taking care of family after a windfall: "You will come to understand that you were taking care of them because it made YOU feel good, it made YOU happy to see them smiling and without a care in the world — and that was extremely selfish of you. While you were feeling satisfied with yourself, you were slowly eating away at their own dreams and ambitions. You were adding material things to their lives, but subtracting the most precious gifts of all: independence and growth."

https://www.theplayerstribune.com/en-us/articles/kobe-bryant...

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

#220
According to one survey many rich people who lose most of their wealth have two causes (1) divorce (2) bad investments advice.

The 1st comes not only for lifestyle changes but also the fact that your spouse may realize she can easily just live by her/himself in case a severe disagreement occurs and hence there are less chances of negotiations and moving on.

The 2nd happens because money managers, wealth advisors are going to swarm you. All your friends and their uncles are suddenly going to have once in life time gold plated locked in deals.

So my advice would be to keep life simple, don’t advertise your wealth and don’t rely on managing your wealth anyone but yourself. Remember Warren Buffet stayed in same house and didn’t even told his family even when he became one of the richest person. Study all your investment options intimately, think of it as your new job. Avoid investing more than 5% of your wealth in any single option that is not backed by government guarantees directly. Make friends with other people with similar networth and learn from them.

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