James put Benjamin to work setting type, cleaning up, and making deliveries, just like any other apprentice. They printed all kinds of things, from almanacs to sermons. Benjamin worked hard and learned quickly.

In 1721 James decided to start a newspaper. At the time there were already two newspapers in Boston, but this newspaper, the New England Courant, was different. Instead of reporting on news from Europe, the Courant reported on local news with clever reporting and contributions from its readers. This combination often meant that some of their material was controversial. Unfortunately, not everyone thought this was a good idea.