Kailasam was born in a Tamil family in southern Karnataka, India. His father, T. Paramasiva Iyer, was employed as munsif in the Mysore state service and progressed to become the Chief Justice of the Mysore High Court. His father’s brother was the Madras High Court judge, Sir T. Sadasiva Iyer.
Kailasam had a good education and was supported by the Maharaja of Mysore to study geology in London. Kailasam repeated several classes to have an excuse to extend his stay in England. He spent six years in school there, participating in theatre whenever possible.
Soon after his return, he joined the government geology service. He became disillusioned with a government job and quit to write plays and live a bohemian life. His father’s failed ambitious plan that he would become the Director General of the Geology Department led him to stop talking to him.