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

The problem is that the industry is littered with con artists and the downside damage an unethical person can do to your finances is horrific.

The best thing is to read, read, and read more before even looking for outside consultation on any of these matters.

Friend of mine in his 60s who was semi retired for the last 15 years had all his brokerage accounts emptied by hackers this year. He might get his money back, but might not. Make sure you use 2fa for all accounts. I prefer RSA secureID where you have a detached fob. Your phone can be hacked and hackers can then get verification codes.

Dont invest in anything except (almost) guaranteed returns for now(1 year CDs are starting to pay 2-3%) .

An emergency fund of 2+ years expenses in cash.

Slowly increase your standard of living over a long period of time (or not at all). I operate from a budget, not from cash in the bank. Religiously stick to the budget (this is hard) but dont beat yourself up if you go over. Quicken does a reasonably decent job of setting up a budget and allows you to keep spending in various "accounts" under control.

The standard safe withdrawl rate is 3%. Im planning for a more conservative 1.5% approach. This means you can take out up to 3% of your total funds each year and never run out. At 8m and 1.5% safe withdrawl you still need to work.

The strategy requires you to have a reasonably significant percent in the market. While the market could keep going up, I think you can wait a few years for the inevitable recession, but eventually you will have to get it into index funds.

I make a good income from my business and it is easy to get sloppy when I have too much cash. Last year at a fundraiser I got drunk and dropped 30K. Im not mad about the donation, but Im mad about the way I did it while being out of control.

Also this account is an example of a wasted $100k :)

I recently went through a major liquidity event myself a few months ago (Wombat Security Technologies). Here are some things my wife and I have done:

- Get a financial advisor. Make sure that they have fiduciary responsibility, that their job is to help you, rather than just fees. Talk to several different ones and find one that you're comfortable with. Note that you will eventually have to spend a fair amount of time learning about all the different kinds of investments that are out there. One surprise for me: I already knew about diversifying your portfolio, but had previously only heard about doing that based on assets. It's also useful to diversify over time too, that is slowly add more investments over time, rather than doing it all at once (since that's timing the market, and you might get lucky, and you might not).

- Get an accountant. You will absolutely need one to handle the taxes.

- Read up on Qualified Small Business Stock. If your company and length of your stock ownership qualify, it could be a quite large benefit for you regarding taxes.

- Set up a Donor Advised Fund. Ok, it's probably too late if you already got the money in the bank, but this would let you donate the stock in a way that would save you a lot on taxes, and allow you to direct money to charities you and your family care about.

- Get this book: Silver Spoon Kids. Our financial advisor got this for us, and I found it incredibly helpful as to how to talk to kids about money, especially to make sure that they don't end messed up. This can be quite common among financially well-off folks.

- Set up a last will and testament. This should be done after you have kids. It's no longer just about you, you have your kids to think about, and what happens if both parents meet an untimely end. You will want a probate lawyer to go through this process.

- Max out your insurance, ie auto, home, etc. People with money can sometimes be targets for lawsuits, for a variety of reasons. Maxing out insurance will help with a lot of things.

- Also echoing a lot of the previous advice, take things slow. Don't make any rush judgements or investments. Time is on your side, and besides taxes, there's no rush here. The interest you would get from just a money market fund will be ridiculous.

Also, the big surprise for me? Well, as you can see above, managing a windfall is actually a lot of work. But think of it as an upfront investment, to make sure that things go more smoothly later on.

Good luck!

Don't do anything sudden, as others have said. But as you start to adjust to this, you may realize that there is something, or a few things, that you have wanted to do, but never could because of money. That place you wanted to go on your honeymoon, but it would have cost $2000 more than you could afford? You can go there now, on a second honeymoon. Take in a game at Yankee Stadium, even though you live in the Bay Area? You can do that now.

There may be several such things. Most of them don't take that much money (from your current perspective). Pick one of them and do it. (Note well: don't go do everything that you've ever wanted to do but couldn't afford to do. As I said, pick one.) You don't have to do it right away. It can wait a month, or a year, until it's sunk in that it's OK to spend a bit more money than I used to. Not a lot - you don't want to drastically change your lifestyle. But you also want to have some benefit from the money. When you've adjusted to the point that you feel free to spend $2K or $10K on something that you've wanted to do, but couldn't, well, go do that.

And now a negative: Pay attention to your marriage. As others have said, spend time with your kids, but don't forget your marriage. Bluntly, your wife can now afford to divorce you. Do your best to see that she never wants to.

Great advice right here. Pretty much every philosopher worth his/her salt will point out that money and power can't buy happiness...but feeling like you are making a meaningful difference in some way just might