Hollingbery's earlier career was spent investing in and starting up businesses, the best known of which was veterinary chain Companion Care, sold to Pets at Home in 2002. In 2005, he began a property investment business, run from his Alresford home.
In the 2010 general election, Hollingbery contested the new constituency of Meon Valley in Hampshire, created as a result of boundary changes. He was elected with a majority of 12,125.[6] He was re-elected in 2015 and 2017 with majorities of 23,913 and 25,692 respectively.
Hollingbery was interviewed for the 2017 documentary Theresa vs. Boris: How May Became PM, in which he was also portrayed by Daniel Casey in dramatisations.[10]
In January 2021 it was announced that Hollingbery would be appointed as Her Majesty's Ambassador to the Republic of Cuba with effect from early 2022.[15] He presented President Miguel Díaz-Canel his letter of credence on 11 February 2022.
His tenure in this position will be ending in March 2025, where he will be succeeded by Mr James Hooley OBE.[16]
Personal life
Hollingbery is married to Janette, originally from America. They have three children together. A horticulture hobbyist, his garden has been featured on the television programme Gardeners' World.[9]