Simon has worked in the newspaper and magazine industry since the mid-1980s ‑ publishing with a MacPlus and an Apple LaserWriter. After life as a magazine and newspaper sub-editor he began implementing editorial systems. He published his first iPhone game soon after the App Store opened and earned enough from the venture to buy several coffees. He motivated a team of developers and designers to put together the first Sunday Times iPad app that launched to worldwide acclaim in December 2010. Every Sunday it is the highest grossing iPad app in the UK and was named Newspaper App of the Year at the Newspaper Awards 2011.