Simon started his career in marine insurance 22 years ago, straight after school, working for Willis Faber & Dumas (now Willis). He initially worked in claims and then moved to placing risks. It was at this point Simon identified an opportunity in the growing market for yacht insurance, as he saw there was limited expertise in the sector, which requires high levels of service and knowledge. In 1998, Simon moved to a specialist London insurance broker with a portfolio of superyachts. In 2002, he set up CRS Yachts, a specialist division of a Lloyd's broker purely servicing the superyacht industry. Five years later, Simon completed a management buyout and continued the CRS Yachts brand as a Lloyd's broker. Since that time, the company has continued to expand and acquired another Lloyd's broker specialising in the tech industry.