My grandparents never lived rich… my grandfather’s father did build a fortune in Long Island but most of it was lost during the 1929 crash and subsequent Depression. However, what they did do was save and invest and land values were inexpensive in the late 30s so they bought a house for $3K a few blocks from the bay. They always lived really modestly and volunteered, worked civil service type jobs, required all their kids to work after school and really just socked away every dime they could. When my grandmother retired, they bought a condo in Florida and became snowbirds. Our family still has that condo. After my uncle died (he was left the house for his lifetime), his brother sold it for over $600K. The rest of the Trust after my grandparents died was divided among the brothers and survivors of the ones that were already gone. They were never Hamptons rich though.