The barber-surgeon John Woodall, best remembered as the first surgeon general of the East India Company, lived a rich and varied life that saw him adventuring abroad several times, building a successful medical practice in London and investing overseas. His guide book for young sea surgeons, A surgions mate (1617), was the first book of its kind and it and its subsequent editions remained in use for more than half a century. The book included an influential three-part medical glossary, which borrowed from earlier lexicons but also introduced new headwords and definitions that were picked up by later medical lexicographers. This article recounts the history of Woodall’s life and books, and illustrates how the paratextual features of his publications reflected his growing professional stature.