He participated in raids against the Spanish with fellow privateers James Logan and William Cooke during the 1540s and is credited, along with Sebastian Cabot and Henry Ostrich, of the start of regular trading between England and the Barbary coast.
Commanding the Trinity Gilbert, he joined James Logan of the Flying Ghost and others in raiding the coast of Galicia during the 1540s.
[2] He had organised the first voyage to the Barbary coast, however he fell seriously ill with the "great sweat" and was forced to turn his command over to another captain.
[8] He volunteered to join Martin Frobisher in his 1576 voyage to search for the Northwest Passage being ready to risk his life "to the uttermost point"; his name does not appear on the list of surviving mariners who were paid after their return and it is presumed that he died on the expedition.
[4] His appointment was possibly due to his time with Frobisher and, with two ships, he sailed for Greenland with orders to reclaim the lost colony for the Norwegian crown and convert the inhabitants to Lutheranism.