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I have heard it said that 1MDB fraudster Jho Low was the only person ever to spend a whole billion dollars on debauchery and loose living. And he had to do things like paid dates with Miranda Kerr in order to do it.
Above the "sufficient to endow an upper-middle class standard of living for life" level, the biggest destroyers of generational wealth are division (which overlaps with the 3 F's in that one of the things that divides fortunes is divorce settlements, but the central case is division between children) and confiscation. Investing your entire life savings in pets.com is what retired dentists who think they are smart do. The failure mode of dumb old money is to halve a fortune over a generation by overpaying for mediocre investment advice, which does about the same amount of damage as the entirely standard practice of splitting it between two siblings, and a lot less damage than being in the wrong place at the wrong time when Lenin or Harold Wilson comes calling.
This is why old money tends to be more present in societies where estates can be entailed- prevented from being divided in a regulated inheritance regime. The extreme form is titles of nobility, but you also see a pattern in the US where leaving aside actual robber-baron descendants, who are usually tracked into very high income jobs anyways, you tend to see medium-level old money in unexpected places due to historic preservation laws more than actual wealth generation. This is why newcomers to DFW are surprised that the actual old-school high culture is mostly on the fort worth side, for example- historic preservation status makes it a PITA to subdivide(although it could be sold entirely) some subset of land used for cattle in ~1900, and almost all of this land has oil on it, so a higher percentage of the fort worth elite were elites back when cattle was the main industry.
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