Why wealth doesn't last three generations
Whether you’re preserving or building wealth, this applies to you.
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"Is the saying true?"
Instead of "Not always", I think it should be "not at all".
Rich people can fail 10 times and still be ok, poor people don't have that privilege.
The 3 generation thing is probably a cautionary tale that's repeated over and over amongst the wealthy and to make poor people feel less antagonistic about rich people.
Rich people usually remains rich or become richer because of the privilege they enjoy (better access to everything). Unless they screw themselves over on one big thing, multiple medium things or many small things -- then maybe they'll become middle class or poor -- what's the probability of this?
Even if they do become middle class or poor because of certain bad decisions, the networks they have (e.g. people who can help them out of the situation), would be people most middle/poor people wouldn't have.
So, I think the saying is largely false.
Don't forget to mention that in some countries, the inheritance taxes and bureaucracy are meant to dissolve any family's assets. The richest always come up with creative ways to dodge it.