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At the age of 18, Drummond established IDL Communications Limited a distributor of mobile phones and fax machines. After this Drummond spent three years outside of the UK, establishing and running distribution and new media companies in emerging markets such as Russia and Africa.
Drummond returned to the United Kingdom in 1995. In 1996 he founded Virtual Internet (VI), an online intellectual property protection and web hosting services company. VI was admitted to the Alternative Investment Market (AIM), a sub-market of the London Stock Exchange, in January 1999. In March 2000 combined a £33m fundraising with a move to the official list. In November 2000 Drummond founded RegistryPro, a joint venture between VI and Register.com which created the domain name
.pro. VI was acquired by Register.com in 2002. In 2008, UK2 Group acquired VI.
In March 2000, Drummond founded Xworks Limited, an e-business incubator, which was admitted to trading on AIM in April 2001 with a market cap of £4.4m at 10p a share. In August 2002, Xworks changed its name to Gaming Corporation to reflect its principal business "casino.co.uk".
In 2001, the Telegraph included Drummond on a list of the "The net losers" after the value of his shares in VI fell by £104m.
Drummond was the founder of Coms plc (L.COMS) an internet communications company. Drummond founded the business in September 2003, and listed it on AIM in September 2006.
Drummond was a significant shareholder in Active ISP, name changed to Active 24 ASA, that listed on the Oslo Stock Exchange In October 2004 with a market cap of NOK 270m. Was taken over by Mamut ASA and subsequently acquired by Visma in the summer of 2011 and delisted from the Oslo Exchange.
In March 2005, Gaming Corporation raised £14m, and in May 2005, acquired Gambling.com for $20m. For the year ending September 2006 Gaming Corporation made profits of £2.5m. The US SAFE Port Act made online payments by US customers to online gaming companies illegal, causing a massive write-down in the value of Gambling.com.
Drummond was a co-founder of Betex Technologies in 2005, and now part of Betex Group PLC, a lottery management and technology company with its main operations in China. Liquidators were appointed to Betex Group Plc on 27th November 2015.
In October 2006, Gaming Corporation changed its name to Media Corporation, and sold Casino.co.uk to CryptoLogic for £3.6m in cash in August 2007.
Drummond was a director of Metacharge Limited from September 2006 to October 2006, an Internet payment service provider that was sold to PayPoint plc for £8.4m in October 2006, and in December 2005, Drummond co-founded Shellworks Ltd, which was admitted to trading on AIM as Nettworx plc having raised £10m.
Drummond co-founded FAIRFX (UK) Limited, name changed to FAIRFX Group PLC in March 2014, a peer-to-peer foreign currency exchange with turnover of £700m (2015), which has recently joined forces with Easyjet to launch a Euro VISA prepaid card to its customers. He was a director from August 2007 until November 2014. 
Coms acquired Redstone Converged Solutions limited in 2013. Drummond stepped down as Executive Chairman in September 2012.
Drummond founded Gametech Limited in November 2013. The company changed its name to Gametech PLC in January 2016, it is licensed and regulated by the Gambling Commission. Gametech sells mobile gambling products using the NENX and ProOptions brands. Gametech (Cyprus) Ltd had it Cyprus Investment Firm license suspended on March 31, 2017 along with several other firms that traded binary options.
- PRO http://www.registry.pro/
- Public listing of Active 24 ASA at Oslo Børs http://www.oslobors.no/ob_eng/Oslo-Boers/Listing/New-listings/Active-24-ASA
- Investment in Nettworx http://www.ft.com/cms/s/0/c5857f2e-7033-11da-a1f7-0000779e2340.html#axzz2fRTenSa3
- London Stock Exchange RNS http://www.londonstockexchange.com/exchange/news/market-news/market-news-detail.html?announcementId=11674447
- Nikovova, Maria (March 31, 2017). "CySEC suspends CIF licenses of several FX, binary options firms". FinanceFeeds. Retrieved March 31, 2017.