"Shirtsleeves to shirtsleeves in three generations" is an old proverb — with genuine equivalents found across many different cultures around the world — describing the commonly observed tendency for family wealth, even substantial fortunes, to often dissipate by roughly the third generation after it was originally created: the first generation builds it, the second maintains or modestly grows it, and the third generation, having never experienced the actual work of building it, often loses it. This isn't purely an old folk saying disconnected from real evidence — family business and wealth transition research has repeatedly found patterns broadly consistent with it, with a substantial share of family wealth and family businesses studied failing to persist successfully intact through multiple generational transitions.
What's genuinely interesting, and somewhat counterintuitive, is what commonly cited analysis in this space typically identifies as the PRIMARY causes — and poor investment performance usually isn't at the top of the list. Instead, much of the analysis points toward behavioral and family-dynamics factors: inadequate communication about wealth and the family's values across generations, insufficient preparation of heirs for the genuine responsibility of managing significant wealth, real family conflict (sometimes triggered by the wealth transition itself), and a lack of shared purpose or clear governance structure for making decisions about family wealth collectively.
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