[discardorama]

Beyond a certain amount of money (I'll throw out a number and say, $10M), the incremental gain is not much. The change in your lifestyle in going from $0M to $5M is huge; but from $10M to $15M? Not much. So these CEOs are doing the smart thing (in addition to the nice thing). They know that when they get the inevitable itch to do the next startup, they can count on a stellar reputation and recruit some great talent.

[autism_hurts]

I think a game changer cash position for most people is 2.5MM liquid -- not tied up in real estate.

5MM means you're flying business/first with your family anytime/anywhere. You may have a pied a terre somewhere.

10MM means you're angel investing, vacationing, and not generally "working" anymore.

15M++ means you bank with The Private Bank of Wells Fargo, have a ridiculous line of credit // no checking account, multiple properties, trust, etc.

[refurb]

$5M doesn't go that far anymore. If you're young and you have $5M, you could take 4-5% per year and make it last 40-50 years.

That's only $250,000 per year, pre tax. Good money, but certainly not enough to not have to think about money anymore.

[mikeyouse]

Your $5M liquid would be earning interest the entire time too. With that much money, it'd be 'easy' to make 4% - 5%/year, so you could live on $250k/year and never touch the principle.

[refurb]

That was my point. A good rule of thumb is that you can pull 3-4% out of a investment each year and you will never run out. Increase that to 4-5% and it should last your entire life.

Don't get me wrong, $250K per year pre-tax is a very comfortable lifestyle. However, it's not so much money that you can spend without thought.