As managing director of Internode, Simon has combined technical expertise with entrepreneurial energy to build a national Internet company renowned for its customer-friendly quality of service. Simon has also established Agile Communications, an Internet Protocol-based telecommunications carrier that has delivered breakthrough broadband services to both metropolitan and regional areas of Australia.

In October 2004, Simon was awarded The Bulletin-Microsoft Smart 100 Information Technology & Communications Award, which recognises his role as "a thinker and a doer; a businessman who proudly wears his tech-savvies on his sleeve".

After graduating from computer studies at the University of Adelaide in 1986, Simon was involved in the establishment of AARNet - the Australian Academic and Research Network - a national Internet Protocol-based network that connected universities throughout the country. From 1989, AARNet provided the foundation for the commercial Internet that started to transform the world of communications half a decade later.

In 1991, Simon founded Internode, a privately owned ISP that now provides national broadband services. Since its inception, Internode has carved itself a unique position among the cut-throat competition of Australia's Internet access sector. As one of the earliest entrants in the Broadband ADSL services market, Internode has recorded strong year-on-year growth since 2000, creating a broadband national IP (Internet Protocol) commercial network while preserving the quality service that earns it strong customer retention rates.

Seven years after founding Internode, Simon launched Agile Communications, a privately owned licensed broadband carrier that is exploiting the opportunities offered by Internet networking within the telecommunications industry. Agile began its pioneering existence by becoming the first SA-based company to gain a national telecommunications license in 1998. Using IP-based technology, it has built new infrastructure that achieves price-performance points not available through traditional carrier networks.

Simon's interest in technology is as broad as it is deep. While working in the US in the early 1990s, he was involved in a fun project to create an Internet-controlled toaster. "It lets you burn the toast from halfway around the world", he jokes.

Simon was also a co-founder of the Internet Society of Australia and founding president of the South Australian Internet Association.