Giles is the son of a Canadian-American mother and an English father: Judith O'Gorman and Allen Clarke. He was raised largely in western Canada, though he spent most of his late teenage years living in the southeast of the UK. He had a fairly "normal" upbringing overall - his parents put his paintings on the fridge as a child, attended his soccer games and school plays as a teen, and divorced after his final year of secondary school.
After secondary school, Giles attended university in Canada for hospitality management and followed up with a degree in information technology in the UK, graduating easily both times. While attending university, he frequently was involved in helping close friends set up and staff startups, and gained a substantial amount of business experience doing so. After graduation, he decided that Los Santos would be where he'd like to try to establish a career; between the climate and having an American citizenship, the choice was incredibly easy.
After arriving in San Andreas, Giles spent a great deal of time in Paleto Bay; he instantly felt a connection to the area as it strongly reminded him of his childhood. He spent a full week funemployed, fishing from the beach and enjoying the sea.
Not long afterward, applications for the Department of Commerce and Labour became available; Giles applied almost immediately despite his reservations about the amount of public interaction the job entailed. Despite the fact that he accidentally punched
Josh Zimmerman in the face - twice! - Giles still got the position. He spent approximately a month and a half doing intense work - improving the database and spreadsheets, getting to know business owners, writing legislation - and eventually resigned for a multitude of reasons, including the fact that the private sector was in need of his sort of skills for records management.
At the request of one of his good friends,
Alistair McKenzie, Giles began looking into improving the data management for Premium Deluxe Motors; this quickly expanded to working with the owners of all of the dealerships in the state to improve their processes. As a natural workaholic, alongside taking on a number of personal, pro-bono projects for friends, Giles also submitted an application to the Department of Commerce and Labour regarding taking over ownership of Smoke on the Water once he became aware of its availability.
After a series of negative news articles and public speeches were made about Commerce & Labour, alleging bias, nepotism, and other wrongdoing, the optics of the auction were so toxic that it would have been damaging to the reputation of the Department of Commerce and Labour to award him the license regardless of merit. His subsequent withdrawal from the Smoke on the Water auction prompted a great deal of introspection on his part, and a number of individuals reached out to him to express their support.
Having won the auction in a tie, Giles was awarded the Vespucci location. While he was initially unsure of the location, he came to appreciate the neighbourhood for its charm and he met a number of people on the boardwalk and the pier.