By the time Rupesh was ten, he had his poems published in a column edited by Kunjunni Mash, who has initiated many young minds to literature.
His talent came into notice with his anthology, ‘Penkutty oru Rashtramanu’, that went on to win the Changapuzha Award for the Best Young Poet in 1988. The book became an instant hit with three editions published in the fastest manner ever. The Mathrubhumi Award put him amongst the serious poets. As he grew as a poet, his language was marked as uncivil by many and applauded avante guard by others. To quote from a few would be, Balachandran Chullikad, who said, “For poetry, the era walks with Rupesh” whereas Punathil Kunjabdullah opines, ‘His intense love poems’ - an admirable contribution’. To Rupesh goes the praise for the first Malayalam cyber venture, a short story titled ‘Draculayude Ezhamathe Vadhu’ (The Seventh Bride of Dracula). To a keen literature observer, Rupesh becomes an iconoclast, who portrays the archetypal villain as a saint.
Dampened at the limited audience for poetry, Rupesh moved to filmmaking. He remembers taking up journalism only to meet movie stars. He worked with Malayala Manorama, a Kerala daily, as a sub editor for a few years. Through the Sunday special edition, he brought out the revelations about the death of the naxalite leader, Mathiyazhagan, and features on Azhikodan Raghavan, the leader of the former Communist Party of India and Nandita, the Malayalam poet. He later moved on to become the senior correspondent with India Today. Lately, he headed to achieve his dream in filmmaking.