A successful book publisher, Herman Woolley was a football player and boxer who did not take up mountaineering in earnest until he was forty. After a brief apprenticeship in the Alps, he went to the Caucasus and made several first ascents. He served as a president of the Alpine Club. He joined Hugh Stutfield and Norman Collie for their 1898 and 1902 expeditions in the Canadian Rockies. According to Collie''s biographer, William C. Taylor, "His unselfishness and imperturbable good nature were proverbial, and he himself used to attribute his successses as a pugilist to the fact that the other fellow always lost his temper first."