Simon set up online bookstore Bookpages in 1996 and sold it to Amazon in 1998. As VP Europe for Amazon, he managed huge growth from start-up through to multimillion turnover and hundreds of staff. In 2000 Simon co-founded and became a partner of Episode 1 Partners, an early stage technology VC which managed the $100m Chase Episode 1 Fund. Episode 1 invested in nine businesses, notably the successful Betfair.com.
As an Angel investor, he has invested in Shazam, been chairman of Video Island (now merged with and renamed LoveFilm), Zoopla! (where he is currently a director) and Shutl (currently chairman).
Recently, Simon founded and funded FriendsAbroad.com, a social network for developing language skills and contacts abroad which was successfully sold to Lesson Nine GmbH, operators of language learning site Babbel.com.
Simon is currently CEO of StormForward, an e-commerce conversion consultancy which helpsonline retailers to increase their online sales and profits.
| Company | Date | Round | Size | Participants |
| Shutl | 10/09 | Angel | £500k | 6 |
| NetProspex | 5/08 | Series B | 4 | |
| Shutl | 2008 | Seed | £110k | 6 |