Ask HN: What did you do when you suddenly got rich?

248 points by ThrowHitJackpot ↗ HN
My company just went through a transaction that increased my net worth by >$5M.

When this happened to you - what did you do? How did you handle it? What did you buy and what kind of financial planning/investments did you make?

193 comments

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Standard advice:

- Set aside money to pay taxes FIRST.

- Invest in mostly conservative instruments, as if you were a retiree.

- Keep a small position in risky stuff to capture some growth and get it out of your system.

- Diversify

- Keep quiet about it, don't get talked into crazy investment schemes. Think "old money" rather than "new money."

- Treat yourself a bit, recognize when you've hit "enough." i.e. more doesn't bring happiness. The number is lower than most realize.

- Remember mom, and others instrumental in your success. Everyone else can apply to your scholarship foundation, haha.

If your expenses are "reasonable" you could live off interest/dividends for the rest of your life. Donating time and charity to whatever causes you see fit.

Agree re: put money away for taxes - I've made the mistake of not doing that in the past and it leads to more problems.

As for conservative - general plan is to put enough money into 3-fund portfolio to be 'set for life' - then be a bit more aggressive with the rest. Agree with diversify. Keeping quiet is good - agree re: think like old money.

I do need to figure out how to treat a bit. Today we decided to splurge on $120/visit weekly housekeeping - too extravagant?

I plan to work for the next 30 years because I like it. I'm around 40 - but we'll see how it all goes.

> too extravagant?

Doesn't sound too bad if you've got millions. Those little things add up though in the long term. Just ask MC Hammer. ;-)

https://m.youtube.com/watch?v=rJjKP8vYjpQ

Frank: You get up two and a half million dollars, any asshole in the world knows what to do: you get a house with a 25 year roof, an indestructible Jap-economy shitbox, you put the rest into the system at three to five percent to pay your taxes and that's your base, get me? That's your fortress of fing solitude. That puts you, for the rest of your life, at a level of f you. Somebody wants you to do something, f* you. Boss pisses you off, f* you! Own your house. Have a couple bucks in the bank. Don't drink. That's all I have to say to anybody on any social level. Did your grandfather take risks?

Jim Bennett: Yes.

Frank: I guarantee he did it from a position of f* you. A wise man's life is based around f* you. The United States of America is based on f* you. You have a navy? Greatest army in the history of mankind? F* you! Blow me. We'll f* it up ourselves.

I'm not in this position, I've thought a fair bit about it since it's in the realm of possibility. This is what I'd like to believe I would do:

Buy 30yr Treasury Bonds with enough of the cash to generate ~$200K/year passively for the next 30 years.

Then proceed to continue my normal life. I'd treat the extra income from the bonds like a raise, invest it smartly, buy things as I would normally. Except now I have an immense buffer to stop current work and/or the freedom to pursue other interests.

But I wouldn't change anything in the first year of such a cash influx.

Wait. You'll need closer to $8 million invested at 2.57% (30 yr current yield) to earn $200,000 a year. And consuming that every year means you'll destroy much of the real value of your hoard over 30 years (you're not reinvesting something to cover inflation). Further putting it all into Treasuries is actually riskier than diversifying across multiple assets - foreign stocks, real estate, etc. If we go into an inflationary period and you're locked into a 30 year at 2.6%, you'll watch your fortune collapse and your stipend's buying power crumble.
You might want to consider inflation into this strategy. 100% allocation to 30yr Treasury Bonds at the current rate will continuously lose money until your 200k (plus yield) becomes a buying power of < 40k in 30 years.

US stocks should be part of your allocation.

First off, unless you were really early, you are going to need about 1.5-2M of that for taxes, so plan for that.

That said, I put the remainder of a similar outcome in 60% stocks (VTI 75% + VEA 25%) and 40% short term bonds (VCSH). The stocks give you growth and the bonds give you stability. Rebalance this once a year and you are done. You are financial secure. Don’t get sucked into crazy complicated schemes - simpler and more diverse is better

1) https://www.bogleheads.org/wiki/Managing_a_windfall (the Bogleheads community is great)

2) Read this book: https://www.amazon.com/Investors-Manifesto-Prosperity-Armage... (or anything else by Bernstein, for that matter)

3) Try to steer clear of people/firms who want to manage your money for a hefty percentage fee. They're one step above crooks, sometimes not even. In the wise words of John Bogle, "you get what you don't pay for."

Good luck, and congratulations!

Very familiar w/ Bogleheads and agree that it's a great resource. Will check out the book.

The advisor I'm looking at is 0.35%-0.7% depending on lots of things. Is that 'hefty?' The Bogleheads mentality is certainly that one can do it themselves. I'd like to believe that this particular RIA is plugged in to certain investment opportunities, but not sure it's worth the risk. If I did do that, I might allocate 10% of post-tax money to speculative things like private investments etc.

From what I understand, private funds, especially hedge funds traditionally charge 2% of assets under management and 20% of profit.

As far as financial advisors go, that doesn’t sound insane, but remember if the advisor is investing your money into mutual funds, etfs, private equity, or hedge funds, those will each charge a nice fee on top of that seemingly small .35%.

Good point. However, as I understand it Vanguard's funds have < 0.2% management fee, so hopefully smaller than .35, e.g. https://investor.vanguard.com/etf/fees

But you're right. If manager charges 0.5% and fund charges 0.2% I'm still losing 0.5% of principal and 0.2% of my gains per year.

I don't see a reason for hedge funds. In my mind those are folks who have a proprietary edge on the market due to location, information, or experience.

To me, private equity ("PE") are folks who know how to reshape companies.

I spent a fair bit of time working w/ and for and sort of as a VC - that is a fun lifestyle but their risk adjusted and fee adjusted return is not impressive:

http://www.industryventures.com/2017/02/07/the-venture-capit...

The weighted average of table "Early Stage Venture Returns" shows about 2.5X on money with an assumed period of 10 years.

That's about 10%. When I invested $400k in venture capital in 2000 [timing...] it was worth $250k total return by 2018 - so not as great.

This is true about vanguard fees being low. Ideally your advisor would only use Vanguard, but if they try to get you diversified into more exotic etfs or mutual funds, expect to pay a fee closer to 1% to be invested in that fund.

> But you're right. If manager charges 0.5% and fund charges 0.2% I'm still losing 0.5% of principal and 0.2% of my gains per year.

Be careful with your math here. It sounds to me like you think .2% fee is only on gains, however it also it on your principal.

Here is a concrete example.

You hire an advisor at .35% per year. In one scenario, they invest you in Vanguard S&P 500 for .04% a year. You will pay .39% a year of your principal in fees. In another scenario they invest you in a hedge fund fully, where the hedge fund charges 2% on principal and 20% on gains.

Here you will end up paying 2.35% per year, EVEN if you are losing money. And if you gain money. The hedge fund will take 20% from that. So best case you are paying 2.35% in principal fees, and pocketing 80% of the profit. Worst case, you pay 2.35% to lose money.

Two extremes of the fee spectrum, so likely you will end up somewhere between the two.

Be wary if you advisor tries to push you away from Vanguard and into a different brand (they can have incentives that don’t perfectly align with you). For instance A Charles Schwab advisor might push you to use a Charles Schwab branded s and p Mutual fund with .25% fee on top of his .35% fee. When the actual fund is exactly the same as the Vanguard one that is only .04% fee.

You raise a good point, I am wrong you are right. Of course the costs are on the entire principal, thank you for correcting me.

Investing in PE/Hedge/VC again is not likely for me. So I agree, with an advisor at .35% and vanguard at 0.04% - it's .39% per year. With 10M invested in VSTAX under these numbers, maybe it gains 4% but i pay out .39 or almost 10% of the gains. Far better than the 2% - but we are on the same page.

Agree that the advisors can have misaligned incentives - I trust the two I'm working with though based on relationships who trust them, so I'm fairly certain they are altruistic, a bit.

By the way, really good podcast on Hidden Forces with Ben Hunt for Demetri Kofinas about the "awesome renumeration" for money advisors, as long as you're right :)

The standard advice that is recommended for windfall recipients is to stash it in a savings account and sit on it for 3 months. The goal is to avoid making any rash decisions based on euphoria.

You can use that time to read some books on wealth management. Two classics are The Four Pillars of Investing and The Bogleheads' Guide to Investing:

https://www.amazon.com/Four-Pillars-Investing-Building-Portf...

https://www.amazon.com/Bogleheads-Guide-Investing-Taylor-Lar...

It is also a good idea to not tell anyone, unless you want to be bombarded by requests from family and friends for loans, invitations to invest in weird ideas/schemes, and so forth.

When did you join the company? What percentage did you own? That’s a nice payday, congrats.
I am moderately successful, and thankfully I have accumulated some wealth over the years, as opposed to a single big hit like in your case. Despite I can't claim to be rich, I have been fascinated by understanding how to manage my money better, and hopefully I can offer some advice here.

In random order:

1) Take it slowly. You don't need to rush into investing, buying stuff, getting a new house, etc, all in two weeks. Slow, thoughtful decisions will usually be better than rushed ones.

2) If you are not financially literate, try reading some good books on the subject, and IMHO, not necessarily the most popular ones. Picking the right ones is NOT easy. There are several lists of "best financial books" or "best personal finance books", and reality is that you should read 15-20, and stick to the 2-3 that you really liked.

Financial literacy will allow you to take much more informed decisions about everything.

3) Depending on your age, where you live, and if you have kids or not, you might want to consider "estate planning", a broad category that includes, among other things, establishing "trusts" (legal entities) or similar and granting some amount of money to the trust, in order to get some tax advantage, and clarify what's going to happen to that money when you will eventually die of very very old age.

4) If you know a few friends who are also rich, talk to them and ask them to share their experience with you.

5) Don't tell others about your wealth, or don't be too specific about how much you have. A >$5M wealth creates issues, and provides strong incentives for people to try to manipulate you.

6) If you are married, share this burden with your spouse - I think it's a good idea to keep her posted, to tell him/her NOT to share too many details with friends and family, and possibly to get both of you financially literate.

7) There's a lot of BS around. Be very wary of any advice, including mine. (especially mine!) Be really, really skeptical about any claim by anybody. Remember there's no free lunch out there.

If you are considering investing in a 12% guaranteed annual return, well, let me tell you, it doesn't exist on Earth (both guaranteed and 12% together).

As a rule of thumb, take inflation + GDP * (1 - long term capital gain taxation) as the threshold beyond which you should start to be wary of any claim.

For US, currently: 1.6% inflation + 3.10% GDP[0] * ~0.75 = 3.92%, which means: any investment that is both guaranteed and above a 4% annual return, you should start being skeptical.

8) Try to invest in things that you understand well, or otherwise try to invest in things that are tax-optimized and dumb-proof (e.g. investing in an index is relatively simple to understand, can be done in a tax-smart way).

9) understand diversification. Key to this is that diversification should apply to your goal in life, and your risk-aversion. E.g. if you're 25, you might want to take a bit more risk, as riskier bets tend to pay slightly better over the long run, if you can take several of them (because comparatively less people are willing to play in risky territory). If you are 55, you might want to settle with a more conservative approach. Etc.

10) Big mistakes are usually made when investing in real estate. Try to separate the "emotional", irrational purchase of your main home, with the "investment" part. I wrote about the "rent vs buy" dilemma last year, it might be a useful read to get started. [1].

Finally, if you want this money to make you happier, the thing is, it probably won't, unless you're really really disciplined about it. Mae West used to say "Money isn't everything, if you have it". Once your basic needs are met, it's very hard to use money properly to be happier over a long period of time.

I personally try not to obsess too much about money, I try to use it to buy me "time" more than anything else, and I also try to...

1) Slowly makes sense but I need to diversify - which I probably will do more quickly than slowly.

2) I'm fairly literate financially but need more depth and breadth.

3) Revocable trust and wills are in the works.

4) Asked friends for recommendations, agreed!

5) Agree. I've told one person (outside of work folks who are in the same situation) and that was a mistake.

6) Spouse is fully informed and has delegated all decisions to me. Oooof.

7) Good advice re: expected safe return!

8) Agree investing in simple things. Investing in America or the World with a diversified portfolio makes sense.

9) agree with diversification and risk tolerance as a function of dynamic market.

10) Real estate seems fun but not really - too many societal changes and troublesome renters.

Good point that you 'can't take it it with you' - interesting to see that as an actual issue to deal with.

Great input - thanks!

- Maxed out insurance (home, car)

- Set aside a large amount for taxes, invested it in US Treasury Bond (get an estimate of your taxes from an accountant)

- Got an accountant

- Read up on QSBS (this can save you a lot of money if you got stock when the company was small enough)

- Got a last will and testament drafted and signed. Also asked our probate lawyer about stupid things people do with money, so as to avoid those mistakes.

- Got a financial planner. Also asked about stupid things people do. (At your scale, probably ok to just do standard ETFs and bonds. Note that don't buy in all at once, diversify not just the investments but also by time, so you're not buying all into the stock market at once. This also gives you time to think and reflect about how you want to use your money and what legacy you want, while also getting some returns on investments)

- Set up a donor advised fund (you can donate stock directly to one and get a big tax break)

- Made a donation and got something cool named after two of my long time mentors

- Read book Silver Spoon Kids on how to talk to one's children about money (our financial advisor gave this to us)

- Read a lot about wealth and power in the United States, in particular sociologist and psychologist William Domhoff's "Who Rules America?" https://whorulesamerica.ucsc.edu/power/wealth.html (I stumbled on this by accident, but found it a fascinating read)

Time is on your side here, so don't rush into anything. I was really lucky to have a brother who already had high net worth, so he was able to give a lot of guidance and discussion of tradeoffs.

Umbrella Policy if you live in California.
> Maxed out insurance (home, car)

This isn't a problem I'm ever likely to deal with, but what was the thinking behind this one? I'd have thought >$1 mil in net worth is the time to cancel any insurance you have (maybe not health) on the basis that you can self insure now.

The point of insurance is to protect your wealth in an accident. You actually buy more insurance as your wealth increases, at least I do.
In my opinion the point of insurance is protect your assets you can't afford to lose. Most people cant afford to risk losing their house so they have insurance. However, if you are wealthy enough and can afford losing it then it's statistically cheaper to not insure it since you are not giving a cut to the insurer.
People with wealth are targeted by scammers who file fraudulent claims against them. These fall under the liability portion of your insurance.

It's not about the house or car, it's about that $10MM in your bank people want to go after by claiming that you tripped them and they broke their back.

Definitely not. You want to insure against catastrophes as they can wipe out all your assets. This includes regular insurance (home, auto, health) and personal liability insurance AKA umbrella up to the value of your assets. If you hurt someone, the victim could seek large damages if they realize you are wealthy. Liability insurance can protect you against that.
But you can afford to replace your assets if a catastrophe strikes. Insurance won't help you if you die in a car accident, so you are taking out a negative-net-expected-value deal that protects you against a very slim selection of catastrophes. In my experience, probably protecting from risks that are less likely than dropping dead at random one day.

And taking the risk that the insurance company won't pay out for some reason. And creating more paperwork and recurring expenses to keep track of. $5 mil is a lot but it isn't enough to take eyes off expenses.

If you drive without insurance, hit someone, and kill or severely injure them, you will almost certainly lose most if not all of your assets in the subsequent lawsuit.

If you have a house and it burns down in a fire, you will spend hundreds of thousands of dollars or more replacing it.

If you get rid of health insurance, there is enormous potential downside risk.

If someone is on your property and injures themselves or you accidentally harm someone, they can sue you for millions.

Insuring against all of this and more is almost certainly under 1000 per year. That is a trivial expense for someone with that much money. Even shit ROI on a portfolio is yielding at least a hundred thousand per year in growth assuming this person no longer works. The more money you have, the more insurance you want because you have far more to lose.

Unless you're in the US in which case just your health insurance could cost you $1000+ per MONTH.
...and that's if you never use it. If you actually need health care, prepare to shell out about another $5-$10k until you hit your annual out of pocket maximum.
> Insuring against all of this is almost certainly under 1000 per year.

Um, no.

Average auto insurance premium is $1,470/yr. [0]

Average homeowners insurance is $1,130/yr. [1]

Average health insurance (in 2018, probably more now), was $440/mo., Or $5,280/yr. [2] (And average health insurance will leave a lot of exposure to costs, so you still have a lot of downside risk at that price.)

The idea that you could almost certainly insure against all of that for under $1,000/yr is...wildly inaccurate.

[0] https://www.thezebra.com/auto-insurance/average-auto-insuran...

[1] https://www.creditdonkey.com/average-cost-homeowners-insuran...

[2] https://www.ehealthinsurance.com/resources/affordable-care-a...

At 5M+ it doesn't really matter if you pay $1000 or $10000 for insurance.
Being indifferent to a recurring unnecessary 9k annual expense is roughly being indifferent to 9000 / +4% * 5m) = 4.5% loss of income from investments. If you're indifferent to too many decisions of this form, it's a good way to solve the problem of figuring out how to manage your assets
I concur with your statements. My guess is the poster accidentally omitted a zero, and likely meant $10k.
>If someone is on your property and injures themselves or you accidentally harm someone, they can sue you for millions.

That was a bit of stretch, no? I agree with the other points.

> That was a bit of stretch, no?

No, healthcare costs plus lost wages and other damages for injuries can get into the millions quite easily, and slip and fall injuries are a real legal liability of property owners.

It really isn’t. I’m an advisor and work almost exclusively with clients who have $10mm or more. At that point if you get in an accident or hurt someone and someone finds out that you’re wealthy, there is a reasonable chance they will come after you. I’ve seen it happen and heard it anecdotally.

A $5mm umbrella policy with one of the best insurance companies in the US is like $500/year. I just went out and got a quote on it last week. The best part is if that were to happen, the person suing will have to go up against the insurance company’s lawyers, who are most likely very good.

Even if the probability of that happening was in the low single digits, would you really want to run the risk over $500/yr?

Do not underestimate the value of umbrella coverage. Cheap to get. Expensive to ignore.
> But you can afford to replace your assets if a catastrophe strikes

No, you can't, unless your income is large compared to your assets and not dependent on them.

$1M liability with car/home insurance is less than $500. Anyone with a 401k should have it.

If you end up in a bad situation, getting liquid enough to pay out a big judgement will kill you with taxes.

Deep pockets make you an attractive target for lawsuits.
Because you're a larger, more profitable, target if you're found at fault.
It's absolutely not about the replacement cost of stuff. It's about protecting your assets from lawsuits.
Indeed, for example, mandatory auto insurance in my state is primarily to cover liability.
Insurance makes lawsuits against property it covers -- more likely, because insurance increases chances of plaintiff to get paid.
So your theory is that slightly wealthy people do not have insurance policies?
Agreed, insurance is a tax on the poor.
The part about not buying into the market all at once as wrong and has been known to be wrong for decades.

Several studies to that effect are linked from the Wikipedia page on dollar cost averaging.

I disagree with you: You're talking about what happens under a rational behavior.

If you get a lot of money suddenly, that's not the case. If you invest it all at once in the market, and get by chance high returns quickly, you could start gambing (investing) very quickly.

that sounds like its own problem to address, not a reason to avoid investing your money.
You misread. The advice was to invest over time to get used to the idea, so by the time it’s all invested, they are comfortable with and calm about that size of investment.
No. That was the secondary reason given in the next sentence, not the main reason.
You’ve misread.

“Note that don't buy in all at once, diversify not just the investments but also by time, so you're not buying all into the stock market at once.”

This is the recommendation.

This also gives you time to think and reflect about how you want to use your money and what legacy you want,”

This is the main reason, comfort/acclimation.

“while also getting some returns on investments”

This is saying you’ll get better returns than cash, so the price of structuring your investment for comfort will be somewhat mitigated. It’s not advising DCA or suggesting outperformance of or parity with investing everything up front.

Diversifying by time is DCA.

If it was the main reason it wouldn't be "also".

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So weird I disagree with everything listed there. Just invest in the SP500 and don’t spent money on BS.
that is what everyone is basically saying...
what's the point in diversifying in time if one believes one cant time the market. the only point i see is "piece of mind" in case the market tanks you wont feel so bad.

If one believes

a) one can't time the market b) the market (as a whole) trends up over time

doesn't this means that on average the best time to invest money is as soon as you can (of course there are other reasons to take you time, but I don't see how "diversifying by time" is a good reason as it would seem to imply market timing)

> "piece of mind"

Small typo, I guess you meant "peace of mind".

yes, need to stop trying to write after midnight
It is because if you can't time the market you don't know whether you are in a slump or in a rally. If you stretch your investment in time you partially avoid a possible crash after a rally when you got in just before the crash.
I really enjoy your point :-) but I see things differently. I think stretching your investment means you learn about how markets and investment really works because you will make a lot of mistakes during a period of time.

Rushing into market means you will make less mistakes, but bigger ones.

(comment deleted)
I like this observation that you can take time to ease into it. A lot of the risks of investing passively are really on the individual and the right mental approach is extremely important too.
Thank you! This is quite good detail. I especially appreciate that you told me what you did - versus what I should do :-)

Insurance is maxed out. Agree that putting tax money in super safe savings method is good.

Got an accountant, not sure it's the right one but not a bad one.

Working on trust and all associated works.

Interviewing various RIAs. Not sure about DAF - I get it but may wait to donate money.

Great book recommendations!

The only question I have for you and others is - what about diversifying? Details on my 'wealth increase' is that company illiquid stock turned into liquid stock; so did you focus on diversifying or patience?

(comment deleted)
There is some really good basic guidance on dealing with windfalls, available on Reddit's personalfinance board: https://old.reddit.com/r/personalfinance/wiki/windfall

I recommend you read it all and take some time to digest it.

Don't do anything rash -- in fact, don't rush to do anything right away unless it's necessary. Necessary things include:

* Figuring out what your tax obligations are.

- You should get someone to recommend you a competent CPA who has dealt with this situation before. You want someone who will proactively help you sort out your tax situation starting NOW, not wait until tax time. But I would _not_ suggest a "wealth manager", or even a "financial advisor" at least to start with -- find someone who will just help you with the immediate tax consequences, and who will deal with you on a flat-fee basis with price given up front. A competent CPA should probably be able to handle this on a bare-bones basis for less than $1000, but _if_ you can get someone who comes highly-recommended and has significant experience with the specific issues you're facing, and can help you navigate the situation, paying a small multiple of that for more good advice won't kill you.

- Note that you are going to owe estimated taxes, which need to be paid quarter-by-quarter, not at tax time. At the federal level, you will not be subject to penalties, regardless of your income this year, as long as you prepay (in payroll withholding plus estimated tax payments) 110% of _last year's_ tax obligation. However, if you are in the state of California there is no such safe harbor for _state_ taxes if your income exceeds $1 million in a given year (which it will). (See https://www.bdcocpa.com/resources/articles/43 .) So make sure you pay California estimated taxes as promptly as you can manage. (But also, don't panic if you end up being charged penalties. For stuff like this (i.e. not fraud) they are generally quite small relative to the amount of taxes owed, especially if you aren't that late.)

* Figuring out your liquidity situation:

- Are you getting the money in cash, or liquid securities (i.e. that you will be able to sell easily), or illiquid securities (i.e. that you cannot reliably sell?) If your employer has been thoughtful towards you, you won't be in the third situation, which can be very messy come tax time. (If you are in that situation, there are people who can help advise you, but you'll want to start thinking _now_ about how you'll pay the taxes.)

- If you're getting securities (i.e. stock shares) that come to you in some sort of brokerage account, it's fine to _leave them there_ while you decide your next steps. Make sure you're able to sell enough to cover your tax bill, but you don't need to actually sell anything until you discuss it with your tax advisor.

- If you're getting cash, you will probably want to open a brokerage account to put it in (don't stick it in your checking account.) Charles Schwab and Fidelity are fine general-purpose brokers. Vanguard is good if your plan is to invest the money in low-fee index funds and then not touch it, which is generally a wise idea.

Oh, and don't post all over the internet about it. ;-) But I see you're using a throwaway, which is a smart move. As the reddit PF link will also tell you, don't go around telling everybody about it. In fact, for now don't tell anybody but your spouse (if applicable) and your tax advisor. You can always tell people later, but you can never un-tell someone. You'd be surprised (or not) at how people can get when huge sums of money are at stake. Even if people know you are getting an IPO windfall (or what have you), be vague and downplay the amount. Don't promise anybody anything. This goes 10x if they are asking you to.
> for now don't tell anybody but your spouse

Depends. One could not mention it at all, and spend their 9-5 at a some-what serious fictitious company where you work on your dreams, but 50% of the time just hang out with your best friends.

But if your story leaked, it probably wouldn't go over as well if your spouse was going to a difficult job every day.

I’m going to assume you’re not married. That’s a horrible idea.
How much of this did you follow when you made millions suddenly?
I like this finance website. Some of the advice surrounds improving your financial standing, but much of it is just about how to live well, and how money does and doesn't play into that.

https://www.mrmoneymustache.com/blog/

It depends on your goals and lifestyle.

$5mm+ is tremendous. Could last you a lifetime. You could try an annuity. Pop this formula into Excel or Google Sheets: =pmt(3%/12,50*12,5000000). A very conservative 3% annual growth rate can afford you $16k in monthly withdrawals for 50 years. The downside is, of course, you'll be drawing down on your wealth til zero.

Purchasing real estate for the rental income can yield more attractive returns. First off, you can leverage yourself up. Then cash-on-cash returns - in well selected locations - could be in excess of 10% (easily). Your principle in real estate is afforded some level of protection and may even grow as the economy and country grows ..standard investing caveats apply.

I was in a somewhat similar circumstance via a very large inheritance. I'll start from the emotional side of things before moving into the financial side.

Emotionally, I was very shocked as I did not see this situation coming. Like you, I was also scared about making stupid choices. You probably had some idea that your shares had upside potential, but the money I received dropped into my lap with no warning and was approximately the same amount as what you received. My immediate advice is...do nothing. Wait for the shock to wear off and for you to acclimate to the situation. Don't tell anyone, don't run out and buy things, don't move assets; just keep on with your day to day life until you are ready to proceed.

Based on the fact that you are here asking these questions at all, my assumption is that the money likely will not change you much as a person. I still have the same friends and relationships that I had before I received my funds; my values are still the same; I'm still the same person. Most people who interact with me have no idea that I am as wealthy as I am. Who you were before you receive your money will largely be who you are now that you have received your money.

Economically, my general spending patterns have remained largely the same. The main thing I've found is that money is less about buying stuff (which I think is how most people without money view money) and more about buying time, cutting through bullshit, buying access, and creating opportunity. I feel much more free to spend money on education, conferences, vacations with my loved ones and friends, once in a lifetime opportunities etc. I'd encourage you to think about your funds this way too depending on your circumstances as I think it brings a lot more happiness than buying tons of shit you don't really need, a big house, cars etc. I'm not saying you need to live a frugal life, but I think excessive consumption gets boring quickly. You have "fuck you" money which gives you enormous power over how you craft your career and your life. Think hard about what you want to do. I still work but I've had the flexibility to explore career arcs that I would not have otherwise been able to with almost no risk.

I would be very careful about telling other people about your situation because it might alter your relationships. I think it's fine to say you are doing well at work, but definitely do not tell people you have 5 million dollars. You don't want people feeling jealous, resentful, etc. It can be helpful to have other wealthy people to talk to about issues and feelings. If other people you trust have money, feel free to talk to them. Alternatively, there are certain places that generally cater to the wealthy (eg social or country clubs, business associations, etc) where you can meet some people who will be in similar circumstances and will be happy to talk.

Moving on to what to do. I don't know how old you are or what your future earning potential is (meaning is there another chance for a payout this size), but in general what you do with five million dollars will not be dramatically different than what you do with a few hundred thousand dollars. I would seek out a wealth management group for a consultation. Make sure this entity is a fiduciary and are legally obligated to act in your best interest.

If you don't think you have more big payouts coming your way, then your strategy will likely focus on wealth preservation. If you think you can make more money you can be more aggressive. Either way, you will probably construct a well balanced portfolio of low cost index funds. Depending on your risk and needs, you could devote a portion of your portfolio to more exotic things like hedge funds or private equity or whatever. See what they say.

You have generational wealth, so if you have kids or are thinking about kids, you need to focus on general tax minimization and avoiding inheritance taxes (within the law of course). There are a variety of strategies that can...

That's very kind of you to suggest it won't change me. I hope you're right and expect you are.

Totally love the idea about buying time. Not entirely clear about what to buy access for, but I'll ponder that.

Agree re: confidentiality. Age is 40, and expect to work for another 5-20 years or more.

Working w/ an RIA so things should be good there, totally agree they must be fiduciary.

Agree long term planning; not exactly sure that giving kids money is a great idea. Perhaps some/all college and help w/ house down payment - but life is a struggle (jihad - I'm not Muslim but that's the analogy I use). Agree learning how to teach them is a good goal! The Silver Spoon book looks good for that!

Check out the FIRE (/r/financialindependence) and FatFIRE (r/fatfire) communities on Reddit. FatFIRE is likely most relevant for your situation.
Check if your windfall qualifies for QSBS. Could save you TONS in federal taxes.
The parent did not market this link enough but OP please read it! Especially if you are not already on your path to financial independence or not really bothered with investments.

This is a writing about people suddenly got money and how they got destroyed by it and how can you avoid it. What can happen in your family because of it. How and why to be quiet about your wealth.

Entertaining and great read and always the first thing I remember when somebody wishes for a jackpot.

You're right, I could have done a better job explaining what this is about. Thanks for doing that part for me!
I've read this before. And it's good, but it's more about what to do if you make >$100M. It strikes me as something somebody writes from hypothetical, not from experience.
I got some hot cash several years ago unintentionally. After that, I set up 3 goals:

1. Maintain high quality life

2. Improve skills for my career

3. Meet more interesting friends

With these three goals, I did these:

1. Maintain high quality life

  1.1. I bought myself a lot of insurance, both financial and life
  1.2. One nice apartment
  1.3. Put about 20% to some low risk fund
2. Improve skills for my career

  2.1. Best keyboard, chairs and ... as a developer
  2.2. Books
  2.3. Donate some open source projects and make friends with contributors
3. Meet more interesting friends

  3.1. Host regular meetups of great developers in China
  3.2. Go to a nice gym as I find people who work out hard and keep self-discipline are normally class-a players
  3.3. Get much more opportunities when focusing on what's next than what you're paid
These are all things you can (and should) do on a regular software engineer's salary, don't need to wait for a $5m windfall.
Depends on what regular software engineers in that area make. I had to basically sell a startup to afford a nice computer desk and chair, lol.
Maybe hot cash means something different, but it means stolen where I come from :)
- Paid off the mortgage - Bought another section, built an ideal house on that over a couple of years - Went to Disney World, took the nieces and nephews to Disneyland (yeah, I'm still cheap) - Sent mum to the UK for a holiday

10/10 would slave away at a startup again (actually that's a lie, once was enough). We didn't owe any money other than the original mortgage, so there wasn't really anything else pressing to spend it on. Already owned a number of guns, motorcycles, and a basic sports car. No real plans to spend the rest, it's in the bank/bonds.

Basically I'm still living the life I always have, I just have a giant workshop now in which to play with my toys and pursue my hobbies. I think if this had happened 15 to 20 years earlier in my life, I'd be looking at things differently, but at this point I just plan to retire a bit earlier than I would have and not change much else. My father was also very savvy financially, I suspect he would have some pertinent ideas.

I now work for a small company as an integral cog in a relatively low pressure environment. I get to build things every day, come and go as I please, and my contributions are respected and valued. It's lovely :-)

Paying the mortgage is usually a bad idea. Assuming we are taking about the US, mortgage interests are tax deductible up to 750k (there are also deductions in most other countries), you already paid the mortgage origination fee, and usually you pay an interest rate that is not too high (if it is, you should consider renegotiating your mortgage, rather than paying it off).
From a pure math perspective, sure. But clearing the mental weight of a mortgage off your list of liabilities has value in itself to a lot of people.
I probably won't pay off the mortgage as the interest rate is 3% and I think I can probably get better return in the market.

Startup is a neat idea. Agree re: banks/bonds.

I like your approach - keep on doing what it means to be happy, and work in a good environment with people you like and who like you. Good for you!

I have not gotten quite that lucky, but still lucky to catch a unicorn early enough to have gotten to ~1m at a youngish age.

Have you actually liquidated the funds? Or is that the value of your stock? I think a more interesting question for this audience is what to do when you have pre-IPO "unicorn" shares. On one hand, if you wait til IPO there may be a big "pop". OTOH, it could drop below what it's trading at in private markets. I think about diversification a lot too.

I haven't felt the need to hire a professional at this point, just put most of my liquid NW into a robo advisor (I use the Schwab one) and forget about it.

A couple years ago I came into about $200M (seriously), and let slip more than I should.

Really it just turns every conversation into a roundabout request for money. People are definitely nice to you and ask you onto all kinds of boards, funds, etc.. but it’s a hassle. You start to worry a little bit at least about personal security, especially if you have kids. You also worry about ruining them forever. (Also, watch out for temptation that could ruin your happy family life... suddenly you’re extra “attractive” it seems.)

On the bright side, you can try and get really big projects done, Elon musk-style. Just knowing you have the money helps a lot in getting meetings, raising more money, etc.

I’d just put it all in an s+p 500 index fund. Though of course I haven’t followed my own advice. I wouldn’t worry too much about dripping it in either, maybe put half in over a month and the rest over six months. Long term you’re pretty likely to wish you’d invested sooner rather than later.

Set up some estate planning stuff and buy a model 3!

I’d just put it all in an s+p 500 index fund

That's a lot of money to invest in the health of one country's stock market -- a successful terrorist attack (think a dirty bomb in NYC or even multiple cities) could wipe out a significant portion of that overnight - it will likely recover eventually (as it did after 9/11), but that's a time when you'll want access to your money

I'd diversify across countries, and maybe precious metals.

Yep, foreign real estate is a good way to do this, and also gives you a passive'ish revenue stream
Many of the companies on the S&P500 are global businesses whose value is based only partially on the US market.

Also, if something big happens in the US (9/11), stock markets tend to take a hit globally.

That said, I’d still diversify into a few international indexes.

Personally I prefer total market funds to the S&P 500. VT is a good Vanguard fund that provides market cap weighted exposure to global markets.
Actually it looks like I have it about 10% in real estate, 20% public equities, 10% private equities, 20% cash, and still 40%... crypto!
How did you make that amount? Was it also as an early employee at a startup, or as a founder?
Bitcoin?
Yep
Please invest in my ethereum startup: FinneyFor.com. Patent pending.
to quote parent: "Really it just turns every conversation into a roundabout request for money."
I mean, you gotta give it to him, that was not roundabout
Are you willing to share the story? I would hazard a guess that you played around with mining on your old laptop in 2010, accidentally left it running for a while, mined 10k bitcoin, and sold around the top at 19k each.
Saying he came into it makes it sound like inheritance but that's an unusually large amount. Maybe a lottery winner. Or just ambiguous wording and I'm making too many assumptions. Either way, cool for him :)
I'd love to hear more about your big projects! I'd love take on Facebook, or plant a billion trees, or fix news!
Mostly some public transit-type stuff and fixing American democracy! And (embarrassingly) maybe a movie?
I love that you admitted to the movie part! I think there is a lot of personal satisfaction to be gained from using financial freedom to create art, even if it's not quite as easy to articulate to other people compared to the benefits of the other projects you mention. Certainly, it's my primary motivator. No need to be embarrassed!
That's really interesting to know. I suppose if I ever came into that much money, it would be a good idea to keep real quiet about it. Thanks for sharing.
Wow what a dream! You make it sound like you (or almost) spent it all, is that true?
Hey congrats and that's great! Appreciate your perspective and your perspective on how everyone wants to take your money. It's not the same thing, but there's an old essay from the 1920s or so - I can't find it - perhaps someone else can. It talks as advice to a young man about how everyone wants to separate you from your money.

S&P500 fund is not a bad idea, maybe a 3-fund portfolio for me.

Agree on invest early. I moved everything to cash 3 years ago, sadly.