Since 2016, he has regularly appeared on the American reality television show The Real Housewives of Beverly Hills, alongside his wife Dorit Kemsley.

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.

This was Rock Joint Ventures Ltd, formed with Joe Lewis of ENIC Group, a British investment company, and Spurs chairman Daniel Levy.

[1] It also had a private hedge fund that specialized 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.

[5] 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.

[4][8] He has developed successful investments in various online betting operators including Party Gaming, Chinese-licensed Betex, and AIM-quoted FUN Technologies.

[2] His personal wealth was estimated at £180 million in the Sunday Times Rich List 2008,[4] and he was noted as actively supporting various charitable causes.

[10] Kemsley's resignation came just weeks after he had been part of a delegation that traveled to Spain in an attempt to sign manager Juande Ramos, a move that was characterized as "mishandled" and which "undermined the club's start to the Premier League season".

[1][2] 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.

[16] Kemsley stepped away from the club in October of 2011, as the New York Post reported that the owners "apparently tired of the flamboyant Brit, who was long on flash but has to this point been short of substance".

Kemsley and Cosmos Vice President Terry Byrne formed a management agency originally named "Sport 10" to handle the former superstar's merchandising and promotional deals.