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Tim Middleton has extensive work experience in the property development and commercial property sectors. Tim co-founded Madai in 2012, where they served as the CEO. In 2015, they became self-employed as an entrepreneur. Middleton also worked at Intaprop Investments (Pty) Ltd as the Chairman starting in July 2018.

Middleton's longest tenure was at Intaprop (Pty) Ltd, where they were a founding shareholder and director from August 1990 to August 2015. Tim played a significant role in the company's development of large-scale office and industrial precincts and shopping centers across South Africa. Middleton also co-founded Kagiso Property Holdings in 1998, a joint venture between Intaprop and Kagiso Trust Investment Ltd, aiming to empower black individuals in the commercial property sector. Tim held the position of founder and director until August 2007.

Additionally, Middleton served as a Non-Executive Director at the National Housing Finance Corporation from January 2001 to January 2007, contributing their commercial and planning knowledge to the board.

Before their involvement in property development, Middleton worked as the General Manager of Sage Properties Ltd from April 1988 to June 1990. Tim also held the position of Deputy Director of Planning at the Johannesburg City Council from January 1981 to March 1988.

Tim Middleton attended St Stithians College from 1970 to 1975, although no degree or field of study are specified. Tim then pursued a Bachelor of Science (BSC) in Town & Regional Planning at the University of the Witwatersrand from 1977 to 1980. Tim'scoursework included subjects like City Planning, Economics, Sociology, Social Anthropology, Environmental Planning, and Engineering. In 1983 and 1984, they attended Lancaster University to complete their Masters in Systems in Management, focusing on systemic thinking and its application to human problem solving.