He was the father of the choreographer Jane Dudley and composer Margaret Purcell, and was the husband of the motorist Hermine Jahns.

[2] Dudley began working as a part-time reporter and typesetter for the weekly Troy Free Press while still employed at the family store.

In 1898, inspired by an article he had read in the Saturday Evening Post titled "Working Your Way Through College", Dudley began putting-away a portion of his earnings to attend university.

[2] After graduating from Columbia Dudley held a variety of odd jobs, including as a retail clerk, a bond salesman, and an occasional stringer for the New York Times.

During his time covering financial news for the Wall Street Journal, Dudley observed that many of the city's most prominent businessmen were essentially "inept" at dealing with the media.

[4] Dudley was also retained to mount a campaign to launch the political career of Woodrow Wilson, then president of Princeton University.

[2] Prior to the Triangle Shirtwaist Factory fire of 1911, Dudley helped organize opposition to the mandatory installation of sprinklers in warehouses at the behest of another client, the Protective League of Property Owners.

At the time, Dudley wrote that the birth of Jane "incidentally solved our problem as to whether or not we should send our boy to Columbia ... neither of us believes in college for girls.