After securing a place to study English Literature at Trinity College Oxford, Olly became actively involved in the university's dramatic society. Upon graduating he was awarded a scholarship to train at the London Academy of Music and Dramatic Art (LAMDA) and studied there for two years. Upon graduating from LAMDA, Ollly met Gregory Doran - the Artistic Director of the Royal Shakespeare Company (RSC) - and was offered the title role in Shakespeare's "lost play" Cardenio. Doran directed and Olly performed the role to critical acclaim, cited as a "dashing professional debut" for Olly by Mark Shenton writing for The Stage, noted for "a beguiling Cardenio" by Mark Taylor at the Independent and being telegraphed as a "talented young man on the path to future stardom" by Simon Tavener at London's leading theatre website WhatsOnStage. While at the RSC, Olly also worked with acclaimed British playwright Antony Neilson. Other theatre roles followed, including The City Madam at the RSC and I Am A Camera, to name a few. Most recently Olly reunited with Neilson for his original play Narrative in a part specifically written for Olly by Neilson and performed at the Royal Court.