An apocryphal story is that a typical pen of the day leaked all over a contract he had prepared for a large policy, and by the time Waterman returned with a new document, his client had signed with someone else.

[2] Later, 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.

Despite later company literature that depicts Lewis E. Waterman as a golden-hearted innocent, all evidence indicates that he was a tough, savvy, and innovative businessman.

In 1983 and celebrating the company's 100th anniversary, Waterman created the Le Man 100, aiming its products at the luxury writing market.

As Waterman progressed into the modern era, it produced many of the pens that are still available today including the Edson, the Exception, the Philéas, the Hémisphère, the Expert, the Harmonie, the Charleston, the Ici et Là, the Audace, the Sérénité, the Liaison, and the Carène.