Simon is the grandson of Ramsey Crookall's founder. He studied Economics at Durham University and then joined the graduate program at the high yield bond market specialist Hambros Bank, trading for them in Sydney and Asia during the 1990s. He then worked for CIBC Global markets in London before becoming a successful entrepreneur.

Simon co-founded Gumtree and Slando, which was sold to Naspers. He joined Ramsey Crookall in 2012 and currently sits on their board and investment committee.