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Even just in terms of money. $20 million invested is--depending upon your assumptions--something like $1 million/year ~risk-free without touching the principle. (OK, a diversified portfolio is probably going to do better than that but that gives something of a baseline.)

Obviously that's a pretty nice passive income stream. But it's not really have a couple nice homes in prime locations, hire full-time assistants, fly private jets everywhere, etc. sort of money.

1 million per year is a fat budget. You can get close enough to that lifestyle by renting slices of the components on-demand and being more efficient from wasteful (and preyed upon) apex lifestyle.

For instance: private air travel in USA. Find some friends with aligned lifestyles and together buy a high performance twin engine propeller passenger plane that seats 8 people for about 5 million.

There are agencies who will take care of all of the complexities of owning and operating this aircraft and renting it out while you’re not using it. With careful decision making you can bring the aircraft to close to net zero steady state operating cost as the revenue flights paying for maintenance, storage, liability etc. You also get access to a stream of excellent pilots on demand.

These agencies can also book you on a larger plane in their portfolio when you want to go further and for some reason aren’t willing/can’t fly first class commercial.

Real estate is much simpler—tons of fabulous rentals all over the world. And an assistant surely could be hired somewhere for 100k or less annually.

> ... buy a high performance twin engine propeller passenger plane that seats 8 people for about 5 million.

There's an 'aviation YouTuber' who owns a private jet (through his medical supply company?) and puts up videos of his travels:

* https://www.youtube.com/user/gregmink/videos

$1 million/year without working is very rich. You could definitely have multiple houses and full time assistants. I have two houses and part-time assistants at an income of $300k. And most of my time is dedicated to work at someone else's company, owning all of your own time makes them much more wealthy than me.

I'm not really arguing with that. But there's a difference between being very comfortable and money basically being a non-factor even for expenses that the typical person would consider a complete extravagance/unaffordable and cost basically being completely irrelevant.

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