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Re:What I Wish I'd Known About Equity Before Joining a Unicorn by luckystartup on Wednesday January 18, 2017 @01:16PM (#13428702)
You're right, but there's a better way to think about the $10 million, called the "safe withdrawal rate".

If you're 65, a good rate is 4%. This means that if you invest your $10 million in a diversified mix of stocks and bonds, and you withdraw 4% per year, then there's a very good chance that you won't run out of money before you die. See: Trinity Study [1]

If you're younger, you should probably use a more conservative rate of 3.5%. That's still an annual return of $350,000, for the rest of your life.

According to your rate of $110 USD per night, you only need to spend $40,000 per year to live in a four star hotel.

First class flights seem to cost around $3,000. You could fly twice a month for $72,000 per year.

Then you have $238,000 left over for food and entertainment. (And hopefully some charity.)

[1] https://en.wikipedia.org/wiki/Trinity_study

Re:What I Wish I'd Known About Equity Before Joining a Unicorn by ktRolster on Wednesday January 18, 2017 @01:39PM (#13428986)
You should also be sure to save enough for healthcare related expenses FWIW
Re:What I Wish I'd Known About Equity Before Joining a Unicorn by refurb on Wednesday January 18, 2017 @02:43PM (#13429632)
What about taxes?
Re:What I Wish I'd Known About Equity Before Joining a Unicorn by wtbob on Wednesday January 18, 2017 @11:33PM (#13433036)
I think we're talking about after-tax money; unless you live somewhere that has a wealth tax, once you've paid all your taxes on income (wages or capital) then you're free and clear.
Re:What I Wish I'd Known About Equity Before Joining a Unicorn by nemo44x on Thursday January 19, 2017 @01:26AM (#13433559)
Common retirement strategies, like a 401K, differ taxes until withdrawal. So taking out 4% of your portfolio every year upon retirement would in fact incur taxes. Since a 401K is massively tax advantaged in your highest earning years it only makes sense to maximize this portfolio while you can thus delaying, but not avoiding taxes, until a later date when you'll likely pay much less on the income.