He played his first Pura Cup in 2002–03 season against New South Wales, but it wasn't till 2005–06 that Simpson started tasting success.
He played four Pura Cup games and was selected for the Prime Minister's XI against the West Indies.
He credits a stint with Forfarshire in the Scottish Cricket League, during his younger days, as being hugely important in developing him both as a player and a person.
[4] Simpson has a master's degree in finance from London Business School and an executive MBA from Queensland University of Technology.
As of 2024 he is a freelance consultant with Byrne, Camel & Co, and the managing director of Cultivate Agri Partnerships, which specializes in agricultural finance.