The Rich Man's Son — Acres of Diamonds

Conwell contrasts the earned home of the previous chapter with the rich man's son, who can only walk his bride through rooms furnished by his mother, and cites a Massachusetts statistic that barely one in seventeen rich men's sons ever dies rich. The lone exception is a young Vanderbilt, who, on learning his father earned every dollar starting on a ferry-boat at twenty-five cents a day, refuses his inheritance and goes to earn his own living the same way, eventually proving capable of managing the family fortune.

Two comic scenes drive the point further: a Niagara Falls chauffeur laughs so hard at the idea his wealthy employer might drive his own six-thousand-dollar limousine that he nearly crashes it, and a lisping, cane-carrying millionaire's son proves unable to carry his own paper and envelopes twenty feet across a hotel lobby.

Conwell then turns to self-made fortunes built on the opposite principle. A. T. Stewart starts with $1.50, loses most of it on goods nobody wanted, and rebuilds by first asking people what they actually needed before investing another cent, eventually building a forty-million-dollar fortune. John Jacob Astor arrives in America in debt for his own passage. Citing journalist Jacob Riis's 1889 survey of 107 New York millionaires, Conwell notes only seven made their fortunes in New York itself, and most of the wealthiest came from towns under 3,500 people, concluding that location matters far less than who you are and what you actually do.