Simon grew up in the family-owned financial publishing business, McGregors Who Owns Whom. Often family gatherings in Cape Town where the company was based would turn into board meetings and vice versa. He spent the first years of his career in the business consumed by financial and company research. When the online version of the family business was sold to Naspers he broadened his experience by founding companies involved in investor relations, bulk share dealing and shareholder administration. This took him to the City in London in 2009 where he added share registry and cross-border listings to his experience. He couldn’t stay away from Africa for too long though and returned his focus to the continent in 2012 with the launch of a new venture focusing on financial research and capital raising.