Pillai gave up his studies after high school matriculation and took to book-selling as a career; he set up an English bookshop, the first such in Thiruvananthapuram, by the side of the main thoroughfare of the city; he used to import English books of every kind from publishers like Blackies & Co. and Longmans Green & Co., etc. in the UK and also Western musical instruments like Piano, Violin and cello. Having grown up as a socially prominent and notable youth, A. R Pillai (then 24) sought the hand of B. Gouri Amma (then 12). Gouri Amma was born on 9 June 1892 A.D. as the eldest daughter of C. V. Raman Pillai, the greatest Malayalam novelist, pioneer Malayalam dramatist, newspaper journalist/editor and well-known social activist. The wedding ceremony was consecrated according to social rites of the Nair community on 23 August 1904.