Spending five years as a student at Ridley—from 1916-21—Glassco displayed a distinct talent for drama and was a fine athlete. After Ridley, he attended McGill University and the Sorbonne in Paris, before he began his career as a chartered accountant in 1927. In 1936, he joined the Ridley Board of Governors and remained for 30 years. During the Second World War, Glassco was named government controller and then government financial advisor in 1946. He was made an Officer of the Order of the British Empire.
In the post-Sputnik frenzy about education, he presided over the Glassco Royal Commission on Government Organization. He also held a number of important positions in the world of finance, including as vice-president of the Canadian Imperial Bank of Commerce. During the 1950's and 60's he also made time to chair the Ridley Board's Finance Committee. Glassco died in 1968.