He was educated at Atholl School in Rayners Lane, Harrow. At the age of 15 Kemsley worked on Saturdays at John Paul Menswear, which led him to meeting Mike Ashley, who opened his first Sports World equipment outlet across the road. They would play darts for money on quiet afternoons.
Career
Kemsley left school in 1984, at the age of 17, and began working at Gross Fine as a junior surveyor. Then, from 1985 to 1992, Kemsley worked as an agent at the commercial real-estate firm Ross Jaye. In 1992, he decided to leave and join his old friend Ashley at Sports Direct where he helped to expand the group. By 1995, Kemsley wanted to start his own business and he established a property and securities company with "the £1,800 he had left in his pocket." This was Rock Joint Ventures Ltd, formed with Joe Lewis of ENIC Group, a British investment company, and Spurs chairman Daniel Levy. Rock was an investor and developer of commercial and residential property, but specialised in land trading. It also had a private hedge fund that specialised in acquiring strategic stakes in public companies, the most well-known being their 28% share in Countryside Properties plc in 2004, which they sold to the chairman for a profit of £12 million. Kemsley was a director of Spurs from 2001, and Vice-Chairman of the club at the time of his departure in 2007. He had helped the club to reach a healthy financial position. Levy announced that Kemsley was resigning to focus on his property interests. By 2007, Rock's property portfolio was valued at £750 million. Lewis parted from the company around that time. It set up a joint venture with HBOS to build a £1bn property portfolio. However, in the wake of the financial crisis of 2007–2010, Rock was placed into administration in June 2009, ending Kemsley's involvement. The administrator PwC began selling the major properties of the portfolio, which included the Selhurst Park stadium, in October 2009. HBOS lost hundreds of millions of pounds, and Peter Cummings, the banker who had promoted the joint investments in Kemsley's portfolio, was fined £500,000 by the FSA in 2012. Kemsley is known as a close friend of Mike Ashley, David Pearl, Sir Philip Green and Lord Sugar. It was through his friendship with Sugar that Kemsley played a part in the ENIC/Levy partnership's purchase of a majority share holding in Tottenham Hotspur. Kemsley later appeared as one of Lord Sugar's interviewer/advisors on the UK BBC edition of from 2005 to 2008. Kemsley was well known as an aggressive player in the property business. In his most successful property deal he bought 27–35 Poultry, an office block in the City of London, for £40 million in May 2006. He then sold it within five months to a former Russian government minister for £72 million. He has developed successful investments in various online betting operators including Party Gaming, Chinese-licensed Betex, and AIM-quoted FUN Technologies. His personal wealth was estimated at £180 million in the Sunday Times Rich List 2008, and he was noted as actively supporting various charitable causes. However, in September 2008 he placed a series of large bets that doomed US bank Lehman Brothers would recover, and in May 2009 the spread betting company Spreadex took legal action against him, claiming that he was liable to pay a margin call of £2 million. In 2010 he led a relaunch of the New York Cosmos soccer club, on the advice of his friend and associate Jeffrey Akiki becoming chairman from August 2010 to October 2011. He installed soccer legend and former Cosmos star Pelé as Honorary President, and in January 2011 appointed former Manchester United player Eric Cantona as Director of Soccer. Kemsley sold his stake in the Cosmos at a profit, and invested in Pele's commercial rights through his agency Legends 10, jointly owned with Terry Byrne who had also worked on the Cosmos revival. In March 2012 Kemsley filed for bankruptcy listing expenses of $34k per month and personal debts ranging from $10M–$50M with debts to creditors including Spreadex, HMRC, HBOS and Joe Lewis. However, Barclays Bank continued legal action in the United States over a £5 million loan to him. In March 2013, the United States Bankruptcy Court initially found against the trustee who had applied for chapter 15 bankruptcy. Judge Peck denied this application, calling Kemsley "a bankrupt who doesn't live like one". However, two months later in state court, Peck denied all of Barclay's claims against Kemsley, saying Barclays had effectively mousetrapped themselves. In a 2014 article in the Wall Street Journal Kemsley discussed how he accidentally got involved with world-famous soccer star Pelé when he purchased the I.P. connected with the New York Cosmos, Pelé's last team. He then flew to Brazil to enlist Pele's help in reviving the brand and from there Kemsley took on the role with Pelé. Kemsleys management agency Legends 10 expects $30 million in endorsement and licensing revenues and has secured $100 million worth of contractual commitments. One of the motivations to secure and promote Pelé was that in the early 1970s one of Pelé's advisers sold his naming rights to the Brazilian instant-coffee company Cacique "for zero," Café Pelé has since become a worldwide brand, and its namesake receives no royalties for sales in the wheelhouse markets of Brazil and Europe. Kemsley is also a talent manager and owner of Nixxi Entertainment agency where he manages pop star Boy George.
Personal life
He was married to Loretta from Portsmouth. The couple have three children and were living in Radlett, Hertfordshire in 2007, before moving to America. His wife and children returned to London in 2012. In March 2015 Kemsley married his current wife Dorit at a lavish wedding in New York City. He has a son and a daughter from his second marriage. Dorit currently appears as a cast member on The Real Housewives of Beverly Hills, having joined at the start of season 7.