He became an investor in the London and Bristol Company and acted as Sir Percival Willoughby's agent and guardian to his son Thomas at the Cuper's Cove plantation in Newfoundland.
Crout was impressed with Newfoundland, and in his letters to Sir Percival Willoughby noted the potential of exploiting its rich resources and the possibility of establishing a fur trade with the Beothuk.
He was accused of being a sympathizer with the pirates but claimed that he only met with them in an attempt to right wrongs done to the colonists and migratory fishermen.
Early in September, 1612 he led a party to within a few miles of Trinity Bay cutting a trail (or "way") as he went.
In July 1613 Crout made a second voyage into Trinity Bay in an attempt to contact the Beothuk.