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John May has had a long and successful career in a variety of businesses. John is currently the non-executive director at Begbies Traynor, and previously held the position of director at Caledonia Investments plc from January 2003 to December 2011. At Caledonia, John was responsible for making and managing equity investments. Prior to that, they were the chairman of The Cook Society from January 2017 to December 2018. The Cook Society is a British-Australian organization that promotes relations between the two countries.

John has also been the independent chairman of AFI Group Limited since March 2014. AFI is a market leader in the UK and Middle East for rental, resale and associated training needs of powered access equipment. In September 2019, John stepped down as Joint Managing Director of Hambro Countrywide plc, a position they had held since January 1987.

John May attended Brentwood School in Essex before receiving an open scholarship to study engineering at Cambridge University. John later changed their focus to law, earning an MA and LLB from Christ's College, Cambridge.