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That's the thing, once you reach a certain level of net worth it's actually relatively hard to become poor again. You have to actively make really poor financial decisions over a long period of time.

Buy a boat for $100,000 and it'll cost you money to maintain and run.

Buy a boat for $100 million and it'll earn you money if you lease it out or take passengers during the 11 months of the year that you're not using it.

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Maybe. It is hard to making money leasing your boat. You need to pay the crew and such. If the market of people wanting to lease a boat is down one year you still have to pay those people.

Note that a boat is a bad example on your part. There are lots of other things you can do that are more likely to earn money.

For that matter if you can afford a $100 million boat, the crew cost is a line item that you can ignore and thus your boat sits in port 11 months just so you can have your boat. If you really like that boat it isn't a big deal that you are losing that much money.

Interesting bit I learned a while back- boat operating costs run about 10% of capital expense, regardless of size of boat.

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