Not much is known about his early life, but it is known that he was born in Rugby, England. Sheriff went to London at some point in his life, and became a grocer to many of the great and good of the day including Queen Elizabeth.
He became trusted by the Queen, and rose to the level of a gentleman, he was granted a crest and coat of arms the main feature of which is a griffin.
He earned a great fortune through his life, but remained childless, and upon his death in 1567, he stipulated in his will that his fortune should be used to found a school "to benefit the boys of Rugby and Brownsover". Which later became Rugby school.
He was buried at the old Grey Friars Church in Newgate Street, London. However no trace remains. The church and all its monuments were destroyed in the Great Fire of London in 1666.