Waterman was working as a pen salesman in New York for a new company founded in the spring of 1883 by a volatile inventor named Frank Holland.

Holland abandoned his company after only six weeks; Waterman stepped in and took over, fitting the pens with a simplified feed of his own design.

In the wake of this and the death of an infant daughter in the summer of 1870, Waterman left his wife and remaining children and moved to New York.

[6][7] Waterman died in Brooklyn on May 1, 1901, and was buried in Forest Hills Cemetery, Jamaica Plain, MA.

[4][5][8] Following his death, his nephew Frank D. Waterman took the business overseas and increased sales to 350,000 pens per year.