Many have written this about this proverb, “From shirt sleeves to shirt sleeves in three generations”.  I will repeat it as it tells a great story about a family who does not address succession with sufficient time and effort.

First generation starts off with virtually nothing but amass wealth.  They usually do it without making significant changes to their cultural values or lifestyle.  The second generation change their ways, often moving to the city, starting large organizations and the family’s wealth plateaus.  The third generation, with no experience of work, consume the financial fortune built by the prior generations, and the fourth generation ends up back with nothing.

An article for consideration here:
Shirtsleeves to shirtsleeves article

This is the classic formulation of the proverb which still very much holds true today.

Learn, think, apply!